Transitioning to Liveaboard -- Younger Person Seeking Your Advice

[Prairie Chicken]

First, congrats on your successes thus far. Obviously you are making good choices, and your logic approaching this idea is very sound. As a boat owner/sailer for 28 years, the biggest mistake we made was waiting until retirement for long-term cruising.

A production boat of about 42' is a good size. Less may be small for a couple or liveaboard. Although you mention you're single, I gather there is also a canine companion to consider. A 10-14 year old boat offers value but also some of the more modern innovations. Boats older than about 2004 actually have wood interiors rather than veneers. Don't be concerned about production boats being ocean worthy. Well maintained, they have taken many around the world.

I see you have pages of suggestions so I won't babble on. Go for it! At your age, you can change direction if and when you desire. Lost time can never be regained, and life can change in a heartbeat.

[ddugger]

As a software engineer you have a unique potential work from home (on water?) opportunity that can jibe well with sailing (pun intended). I have a B-N-L that is a senior Apple software engineer that works from home - so I have some insights into the requirements.

There are incremental and logical progressions that can make the decision for a live aboard life comparatively less risky than just taking the plunge. You seem to be on task in this work flow process:

- Building or buying a small/day sail boat.
- Join a yacht or sailing club and or sail with a friend(s) with boats you might consider owning.
- Some kind of formal sailing instruction and or capt. license.
- One week group charters (depending on your social tolerances).
- One week+ solo charters in or to places to which you have an attraction.
- If at this point you haven't satisfied your sailing itch and or wanderlust, buy a boat that you can live on comfortably for an extended period. I suggest looking at 40'+ catamaran because they have the capacity to not only have a comfortable living space both inside and outside, they have the best laid out (and ventilated) galley and heads, but also the additional cabin space for a functional office - especially if you get the "owners" version layout.

Living aboard can be a rich and wonderful time in your life and I think the younger you are the more rewarding it can be if you have the right mindset - and it appears that you do. I moved aboard my 41' classical ketch that I had already owned for 20 years, after a no-drama divorce from a marriage with adult children of 32 years - when I was 51 and lived there for about five years. It was one of the most wonderful, interesting, educating, self-revealing and unique periods of my life. As a biotech consultant I could make my own schedule and I had an office with one of my clients on land when I needed it. Hurricane Francey took my boat and the floating marina in FL where it was well tied up in 2004. Sad like losing and old friend, but the good news was my boat was insured for more than its resale value and they paid off immediately.

While my esthetic side loves classical mono-hull sail boats with wine glass sterns, swoopy lines and with lots teak, I learned the hard way about their maintenance as a killer of sailing and sail boat ownership - time and money. Since the hurricane I have chartered pragmatic fiberglass cats for a week or more. Had my second marriage wedding on Lagoon 38 in the Grenadines in 2007. Other charters in the BVI and the Spanish Virgins.

At 74 I am still think about owning Leopard 46, which to my needs has the most optimum live aboard layout that exists in this size and price range. My sailing wanderlust has been somewhat tempered by buying a second home in the southern Caribbean where I windsurf and dive almost daily. Even though I am healthy and very active - there is no doubt that living aboard is easier and more attractive when you are younger assuming you are analytical in the process and your head in the right place emotionally.

A final word of caution - research the marinas that allow live aboards in the areas you plan to live aboard before you commit. Marinas and anchorages that accept live aboards in US waters (an in even in desirable foreign destinations) are becoming an increasing limitation in cost, time and frustration.

The old adage about life being a journey and not a destination fits sailing, too. Life is better when well considered, optimizing your desirable opportunities - while reducing their risks, and having as few regrets as possible. Live well - savor and enjoy it daily.

[doctorbill]

I did EXACTLY what you are describing when I was 38 years old and wish I had done it earlier. Lived aboard a 42 foot sloop in Marina Del Rey and worked full time. Did it for about 3 years.

You will learn so much about living on, maintaining, and sailing a boat. I always tell people there is no easier place to live on a boat in a marina than SoCal - due to the weather you're not under extreme hot or cold challenge. That said, you will pay for it in costs. I paid $1450 for a liveaboard slip for a 42 foot sailboat. Nothing was metered (electric or water) however. The slip did come with all the amenities of the apartment place that owned the slips - this was covered parking, laundry facilities, pool, hot tub, gym, tennis courts, showers, etc.

Do know that many marinas do not allow liveaboards, and they will restrict liveaboards to certain sizes and conditions of boats - they want not-tiny (has to be > 38 feet in my case), and new-ish (they asked to see pictures of boat).

This is also absolutely the cheapest way to own a real sailing yacht, as the costs become your cost of living, not just a toy that sits in a marina unused. You can sail the entire CA coast and explore the channel islands.

So I say do it! If two years later you decide to sell the boat you will have a paid a modest fee for a learning and adventuring experience of a lifetime.

And it will DEFINITELY help with the ladies. Are you kidding? It's next best thing to being a musician. Buy a guitar with the boat and you will be flush!

[aManAndHisDog]

So many great comments here. I appreciate you all! It's been a crazy work week so no time to get in depth this week unfortunately but I have been slowly churning through these responses and understanding them.

All of these perspectives are so valuable! If my assets were more liquid and diversified this whole thing wouldn't be a question but since it's tied to my home this is why I'm deliberating, and perhaps over analyzing, this whole thing. So hearing wisdom and advice from everyone is TOTALLY appreciated -- it helps expand the mind and see things in new ways.

@doctorbill I would love to live aboard down here in socal but unfortunately, from what I gather, the wait lists are massive and it's very hard to get in. My buddy is on a 20 year wait list to get a 40-50' end tie at my local harbor! It's nuts! The slip costs don't particularly bother me, but the wait and frustration just finding a place is crazy! I think there is *one* harbor in SD that's NOT near the airport or the 5 that I am looking into, but they require a nicer bigger boat so we'll see.

@ddugger:

I totally agree. I was originally looking at Lagoon 42's -- that was what I wanted and that was it! The price won't work for my first plan (keeping the house) and it's a pretty big chunk to bite off for a first experience. I could swing it though if I really wanted it. Perhaps as my picture of what I want to do clears up and I get more sailing experience that can come into play, but at $350k+ for a chartered boat and even more for an owner's version they are pricey, and pretty tough to find in the US without hurricane damage. I totally agree though, these appeal to me way more too for live aboard. Especially someone who wants to bring surfboards everywhere -- they can just live in one of the hulls! There's a new-ish Lagoon 42 in my harbor that I've kayaked around a bunch dreaming about owning it haha! I'm hoping one day I can bump into the owner and offer to crew for them or see if they'll take me out on a sail. I think these boats look so awesome. I could see myself sailing the BVI and surfing all along the way -- I've been dying to surf down there!

[billdomb]

Originally Posted by thomm225

Why don't you buy a boat for $5,000 to $25,000 and see how you like it?

Don't waste a ton of money on a sailboat that you might not even enjoy.

And be careful with the opinions you get on a cruisers/liveaboard forum.

Some of these guys are liveaboards and hang out at the dock just waiting for someone to talk to.

It can be a bit strange.......

Also learning to sail is important also.

On target here! There are plenty of boats at relatively lower price points, especially if you're not contemplating a lot of deep water passages.
Two things: ask yerself "What's the worst that could happen" and what might be exit strategies if things don't work out.

[Wander4Wonder]

This thread speaks to me. I am 44, have longed to travel since I was a kid, I grew up on lakes in aluminum lake boats but didn't find sailing until I was older and participated in a few charters. While my friends were up in the bow taking instagram shots and drinking cocktails I was at the helm annoying the skipper with questions and poking around in lockers looking at wiring and storage and looking at how things operated. I've convinced friends to go sailing with me just to have more opportunities to be on the water and get more exposure (to the point of getting really angry at a couple who didnt want us to keep heeling and going 12knts in a regatta race amongst a group of charters. I've been to 6 continents with the exclusion of Australia but want to visit so much more.

As I've gotten older, I have advanced in my career, in my financial security, but never my fulfillment. I saw my Dad a Naval Aviator turned airline pilot who was always so physically large get eaten away by Parkinsons and Llewy Dementia and lose any hope of enjoying his retirement. I don't want to have those regrets, I don't want to live an life not lived purposefully, but I still am anchored by fears of doing it alone, or doing it and failing or doing it and becoming destitute.

Just before I lived in London 6 years ago I started getting really into the youtube sailing vlogs and while I was awed by the exotic locals and the slick video work, it wasn't those things that really caught my attention (ok the beautiful women didnt hurt ) but it was the technical episodes and the details on the process and culture of sailing/cruising, the enjoyment, the organization, the self-reliance, the understanding how things work or how the world and the oceans work. To the point as a project manager and a bit OCD on organization (without going overboard) I started a plan including the courses and skills I need to learn, a budget, lists on lists of things to consider or plan for. List of names, lists of equipment, lists of medical gear, lists of spare parts, power management. I've poured over boat styles, manufacturers, vendors to better understand the ecosystem of sailing...

but I still feel so far away and without progress...I know I am not old but I am not getting any younger and the hours crawl but the years sail by and I can feel the fear that in a wink it will be too late.

Longstory short, I wonder how to go about the next step...with the pandemic I could probably continue to work at least part time or consult to a degree and I could probably move anywhere in the D.C. area to be closer to the water or to marinas (Annapolis is drivable and D.C., MD and VA have options) I am in Alexandria and there is a yacht club here I thought about inquiring about but they seem to require references so its a bit hard to figure out how to crack into the community and being unschooled and my age I don't know if I would be the type to be picked up for crew.

I've thought about buying a slip or two in Baltimore or elsewhere and renting it out just to have it and to meet any liveaboard requirements for the future (most require ownership for 2 years before liveaboard).

sorry for the ramble but its a bit chicken or egg, do I buy a small boat and slip before taking any courses so I have something to practice on docked after having it delivered and or do I take the courses first THEN buy a starter boat knowing that I may take the courses only to have a large gap before I buy. I feel I could continue to plod along and wait until retirement at 55-65 and maybe jump...thats the desire for security, the procrastination and fear and narcissism that time will wait for me to be able to do it or enjoy it at the same level or I can earnestly start changing my life to ensure I at least have the choice to live seeking life rather than trying to die in a coffin of a condo/home with a full bank account made up of the value of memories not made.


""I’ve always wanted to sail to the South Seas, but I can’t afford it." What these men can’t afford is not to go. They are enmeshed in the cancerous discipline of "security." And in the worship of security we fling our lives beneath the wheels of routine — and before we know it our lives are gone.
What does a man need — really need? A few pounds of food each day, heat and shelter, six feet to lie down in — and some form of working activity that will yield a sense of accomplishment. That's all — in the material sense, and we know it. But we are brainwashed by our economic system until we end up in a tomb beneath a pyramid of time payments, mortgages, preposterous gadgetry, playthings that divert our attention from the sheer idiocy of the charade.

The years thunder by. The dreams of youth grow dim where they lie caked in dust on the shelves of patience. Before we know it, the tomb is sealed." - Sterling Hayden - Wanderer

[thomm225]

Originally Posted by Wander4Wonder

This thread speaks to me. I am 44, have longed to travel since I was a kid, I grew up on lakes in aluminum lake boats but didn't find sailing until I was older and participated in a few charters. While my friends were up in the bow taking instagram shots and drinking cocktails I was at the helm annoying the skipper with questions and poking around in lockers looking at wiring and storage and looking at how things operated. I've convinced friends to go sailing with me just to have more opportunities to be on the water and get more exposure (to the point of getting really angry at a couple who didnt want us to keep heeling and going 12knts in a regatta race amongst a group of charters. I've been to 6 continents with the exclusion of Australia but want to visit so much more.

As I've gotten older, I have advanced in my career, in my financial security, but never my fulfillment. I saw my Dad a Naval Aviator turned airline pilot who was always so physically large get eaten away by Parkinsons and Llewy Dementia and lose any hope of enjoying his retirement. I don't want to have those regrets, I don't want to live an life not lived purposefully, but I still am anchored by fears of doing it alone, or doing it and failing or doing it and becoming destitute.

Just before I lived in London 6 years ago I started getting really into the youtube sailing vlogs and while I was awed by the exotic locals and the slick video work, it wasn't those things that really caught my attention (ok the beautiful women didnt hurt ) but it was the technical episodes and the details on the process and culture of sailing/cruising, the enjoyment, the organization, the self-reliance, the understanding how things work or how the world and the oceans work. To the point as a project manager and a bit OCD on organization (without going overboard) I started a plan including the courses and skills I need to learn, a budget, lists on lists of things to consider or plan for. List of names, lists of equipment, lists of medical gear, lists of spare parts, power management. I've poured over boat styles, manufacturers, vendors to better understand the ecosystem of sailing...

but I still feel so far away and without progress...I know I am not old but I am not getting any younger and the hours crawl but the years sail by and I can feel the fear that in a wink it will be too late.

Longstory short, I wonder how to go about the next step...with the pandemic I could probably continue to work at least part time or consult to a degree and I could probably move anywhere in the D.C. area to be closer to the water or to marinas (Annapolis is drivable and D.C., MD and VA have options) I am in Alexandria and there is a yacht club here I thought about inquiring about but they seem to require references so its a bit hard to figure out how to crack into the community and being unschooled and my age I don't know if I would be the type to be picked up for crew.

I've thought about buying a slip or two in Baltimore or elsewhere and renting it out just to have it and to meet any liveaboard requirements for the future (most require ownership for 2 years before liveaboard).

sorry for the ramble but its a bit chicken or egg, do I buy a small boat and slip before taking any courses so I have something to practice on docked after having it delivered and or do I take the courses first THEN buy a starter boat knowing that I may take the courses only to have a large gap before I buy. I feel I could continue to plod along and wait until retirement at 55-65 and maybe jump...thats the desire for security, the procrastination and fear and narcissism that time will wait for me to be able to do it or enjoy it at the same level or I can earnestly start changing my life to ensure I at least have the choice to live seeking life rather than trying to die in a coffin of a condo/home with a full bank account made up of the value of memories not made.


""I’ve always wanted to sail to the South Seas, but I can’t afford it." What these men can’t afford is not to go. They are enmeshed in the cancerous discipline of "security." And in the worship of security we fling our lives beneath the wheels of routine — and before we know it our lives are gone.
What does a man need — really need? A few pounds of food each day, heat and shelter, six feet to lie down in — and some form of working activity that will yield a sense of accomplishment. That's all — in the material sense, and we know it. But we are brainwashed by our economic system until we end up in a tomb beneath a pyramid of time payments, mortgages, preposterous gadgetry, playthings that divert our attention from the sheer idiocy of the charade.

The years thunder by. The dreams of youth grow dim where they lie caked in dust on the shelves of patience. Before we know it, the tomb is sealed." - Sterling Hayden - Wanderer

Yes buy any old small boat and start sailing.

Why people pay to learn to sail is beyond understanding for me at least but I taught myself in a lake in Tennessee after owning maybe 6 power boats that I used to fish in the bay here in the 70's when I was a teenager.

Get something 22' or more so you can overnight if you want so you will understand the whole thing.

I paid $2,000 for my boat and have had it in the lower bay in winds as high as 30 plus knots. I can stand up in it. I can cook in it and solar provides all the power. It also has an autopilot and an ac inverter for my computers and HDTV.

Some have sailed boats like mine round the world. My slip is $243/month. Liability insurance is $10/month.

Get out an enjoy know!

When at home we miss the thrill of a passing squall......but not on a small boat when you have no where to hide.

Anchored near the York River.

https://www.youtube.com/watch?v=okRZs6os5Eo

https://www.youtube.com/watch?v=6gcZKr25UUM

[ScottyMR]

Originally Posted by Wander4Wonder

"...hard to figure out how to crack into the community and being unschooled and my age I don't know if I would be the type to be picked up for crew." - Sterling Hayden[/I] - Wanderer

Wonder4,

This worked for me at 58, You're 44..and you're ahead of where I was.

I found a sailboat club that offers ASA training. I took 101 there. That cascaded into meeting people. Since I first joined I've taken 103 & 104. Shopping for my first boat now.

I'm 60 now. In the last two years, I've had about 150 days on the water. On other people's boats. Mostly on weekends. I've take a bunch of free clinics...well, included with my membership fees. I asked a spinnaker clinic instructor, who is a member of a yacht club, if he knew of any racers that needed crew. I now crew in the yacht clubs races, as a NON-member. Cuz they're always looking for crew. I've met tons of people there.

I've also met tons of sailors at my club. And I've taken tons of clinics for no extra charge, and learned coastal nav, knots, docking under sail...you name it. Like you, I've chartered bareboats with my new friends, and in May, I will be crewing on a 68 foot Swan delivery between St Maarten and Newport.

All that is doable without owning a boat. And without a huge investment.

On the other hand, I met a real nice guy the other day at the yacht club where I race. He's a newbie. Didn't know how to sail. He bought a boat LAST August. Then he joined the yacht club. Then he sold his boat and bought a new one. Then he bought a third boat. He did all that in 8 months. Yikes...good idea to get some time on other peoples boats before buying one...at least me me...but you do you.

You're 44. You're certainly not too old or young to crew. It depends on what you want to do. But you're on CF...so I'm guessing racing around cans on dinghies or Melges isn't your thing. Mine either. I race on an old Hunter 30 racing cruiser. It's a blast. The main thing is that the education and contacts are available if you go poke around. You're in the Chesapeake area...only about a million yacht clubs there. And not a shortage of sailing schools. Probably a lot of sailboat clubs too...like the one I'm a member of. Go knock on the door and talk to people. And maybe join one. In my experience most of them are not the type Thurston Howell III would be a member of...but surely some are. I'm not in the DC/Annapolis area....what do I know. Most of the people I've meet at yacht clubs are super friendly and welcoming....and WANT to help newbies get on the water. I suspect you'll be surprised how soon you'll be on someone else's boat.

Good luck,
Scotty

[thomm225]

Originally Posted by ScottyMR

All that is doable without owning a boat. And without a huge investment.

Good luck,
Scotty

Where do folks come up with the idea that a boat is a huge investment? Can you not afford $2,000 - $20,000 for a boat? I once heard sailing lessons could be like $500 or more.

Without going into all the details, here's my 1974 Bristol 27 in winds that had been over 30 knots while crossing the 20 miles of the lower Chesapeake Bay.

Bought for $2,000 and upgraded over the last 10 years with about another $10K when I felt like making improvements. I was sailing it in the bay a month after purchase. No long refit here. That is ridiculous anyway to spend years refitting a boat without knowing how it sails.

The camera is deceiving the waves were huge and earlier were breaking over the side before I went DDW. It was wind against tide the whole way.

The problem here is I had too much mainsail up and had to steer ......autopilot couldn't handle it due to too much main.....which causes a boat to want to turn back toward the wind.

The sound of the wind in the rigging tells the story ....plus the amount of water the boat is pushing.

Of course, my boat isn't just any boat....it can handle a big wind, downwind sail as long as you can handle the constant rolling without blowing chunks! (which I had to adjust to from my previous experience on power boats and racing beach cats that have a whole different motion)

https://sailboatdata.com/sailboat/bristol-27

https://www.youtube.com/watch?v=-nXfjcCuiPk

[ScottyMR]

Re-read his post. He's talking about BUYING 2 slips.

[thomm225]

Originally Posted by ScottyMR

Re-read his post. He's talking about BUYING 2 slips.

Ridiculous.....

My slip costs me $243/month and I can leave in September if i want.

Done deal and then go get a month to month slip.

Avoid buying until you know whether or not you like sailing.

My marina is full of boats that rarely move.

[nickc]

You are over analysing the issue.
With a good job and a house to fall back on go for it!
If you buy a three year old production boat it could be better than a new one for two reasons.
1. Nearly all new boats have teething problems which have been sorted out by then.
2. Those that can afford a new boat usually enthusiastically fit extra gear in their first few years of ownership and this doesn’t usually reflect in the selling price.
So you could end up with composite sails, spinnakers, water makers etc. etc.

[billdomb]

Might want to connect with Nick O'Kelly who does consulting on this sort of thing.

What boat to get, etc, etc.

Nick is nick@nickokelly.com

Good luck!

[wolfgal]

hey again!


lots of folks have given you fantastic advice here. and yes, it is a lot to process, especially since the term "sailing" is huge and encompasses many different ways to use a boat. you've surely noted how the advice given (as wisdom-filled as it is) usually comes from personal experience. this is because sailing can mean different things to different people. this is also why everyone asks the same question: how are you planning to use the boat?

how to sort it all?

one thing that could help you to get clarity is to ask yourself WHY you want a boat and then again, WHY to that and again and again

from what i've picked up (and i may be wrong, but this is just for thinking), your primary reason for wanting a boat is to live on the water in a marina.
why? from what i can tell, you see yourself being able to thrive there, away from the crazy rat race. you seem to need the away-in-nature experience, to give balance to your on-line work life.

i see you as someone (perhaps an introvert) who wants to be able to filter your relationships with care (invite only those who are willing to understand and respect your choice) and enjoy a small community of folks that look out for one another in the real ... as opposed to living, as convention would have it, in a house, with a yard, with the typical american dream. is this what you mean when you say you want a different perspective?

since you outfitted your truck to camp out and enjoyed this, you seem to enjoy both the camping aspect and the get-out-of-dodge possibilities that boat life can bring. and yes, the wind taking you out of dodge is hard to beat. and, yes, anchorages are hard to beat. living according to the weather. in the elements, rain or shine... big skies of stars.... yes, definitely.

and, there is of course, from there, all the potential challenges that could beyond this, embodied by the sailboat, things to strive for, like taking your sailing learning up a few notches... to learn do long passages, to learn become a really good sailor... not to mention the thrill of knowing that a 'future there' is up to you, if you choose to do so, put your energy/effort/focus there.

i might be off-base, it doesn't matter. the point is that some people have a much different approach to sailing.

this approach may be influenced by personal life choices. for example, let's consider how some prefer to live in an apartment/house (on land) and use the boat during holidays or weekends.

whether they use their boats to go for a daysail or to explore local areas, or to race, or to fish, or to hang out socially with friends, or to eclipse into anchorages for the peace there or escape home life (here, we call it 'boat therapy')..., the fact that they live on land and really use the boat as a tool for these activities (whether they aspire to long passages or not) infuences each's process in the buying of the boat (and yes, the type of boat to choose comes into play according to what you do with it).

the point here is that, in some, if not in most of these cases, it could very well make more sense to start small (with a dingy or very small boat) and move up once the actual sailing skills were aquired. living in a house makes that choice practical and a smart one.

you may ask yourself: does it make sense to start by buying small dingy type boat when moving onboard as a live aboard is my first prerogative?

maybe, maybe not, but this is a good question.

hopefully, my opinion will be balanced by that of others here, but i would argue that, if your first reason for a sailboat is effectively to live on the boat, then it makes sense to find just about any boat (that is in good shape, not to be overwhelmed) that has a slip or that fits a slip you find. finding a slip is tough enough as it is. and you are not going to be able to get a LOA of 42' into a slip that measures 30'. and you need to think about beam length, too.

in my humble opinion, even if it is in a far-off area or even if the boat is not that great with a dog or a bit on the small side, by starting with what is most important in terms of your "use" of the boat, you can begin to satisfy the part of the dream. maybe this primary use is the key, the foundation to the rest of the story?

i imagine that, once you live this way for a while, you will grow and learn and come to know if you want to pursue the rest or not without making changes to your situation in life... in regrettable ways. maybe you will get fed up with doing laundry in a laundry mat or with how much constant maintenance is involved (things break!). after a year or so, you may decide to get a real live-aboard boat or a real passage-maker, or you could decide to move to Portugal with a cute girl you met... and simply move on.

or maybe you will love this part of the experience and find yourself eagerly learning from/helping others, and, from there, take courses, explore other marinas, get on waiting lists and make a clear more-what-i-want plan...

by the way, most people do not buy the right boat the first time around anyway. why learn the hard way? like many here, i suggest that you aim to move onto your second boat (the one suits your needs/wants better), once you know what these wants/needs are.

boat buyers are advised to think about how they plan to use the boat five years from now, but, any way around it, beginners are obliged to take cetain baby-steps until the 'dream' becomes is more clear.

knowing which baby-steps to take is part of the equation to solve. if you ask yourself Why in a deep way, you might be able to hone into the baby-step that makes the most sense.

[Buzzman]

Does your job require daily access and attendance at an office? if so, this will seriously limit the 'freedom'. Where you moor the boat will need to be within easy reach of the office.
If not, then this opens up more opportunities for mooring place. For example, one of the long-term contributors on this site lives in a marina on San Joaquin river, east of SF in the Delta, and there are more remote spots still in the Delta where it is at least possible to find a berth or anchor out.
Years ago, living in Sydney, Australia, I had a colleague in his early thirties who kayaked ashore each day from his sneak-aboard (no living aboard allowed in Sydney). So it is 'possible'....just depends on your risk appetite.
Maybe, if the mortgage is so large, you could get out from under it, buying a slightly cheaper place that your income *could* afford and with a tenant would be cashflow positive....???
The 'home' then becomes just an investment, and so it need not be so 'desirable' to you, and could be further from the office, the city, the boat....the important thing is cashflow...
But yeah, second what others have said. Don't stick all the eggs in one basket until you are certain the liveaboard or cruising life is for you.