Practical options for workiaboard in the Med and maybe flying back to the UK monthly

[mr_rob]

Hi all,
I'm hoping those of you experienced with working on board could critique or help build some possible scenarios that would work.

I've got a job where I could probably agree to only come in to the office for a few days a month, and after completing the RYA Day Skipper/ICC and chartering a a couple of boats I've been thinking about possible options to "work from boat" and would love some suggestions.

Constraints
-UK passport holder - The usual Schengen problem of 90 EU days every 6 months. I also have an Australian passport but I guess they'd figure that out.
- Need to be able to visit London every month for a few days. Maybe a 5 day week. I mention London as it has strong airline links to many airports in the med
-Budget for a boat would be a 40-45ft catamaran of sorts

Scenario 1 idea
-Buy in November at the start of low season - cheaper to buy?
-Winter in Tunisia and see what the boat needs
-Sail around in Summer shoulder seasons
-Put the boat into charter during July/August peak season: attempt to solve the 90 day limit problem get some costs back.
-Potentially work back in the UK during this July/August period
-Winter in Tunisia or something at end of the season
-Happily married with no kids. Age is early 40s

Scenario 2 Negotiate no office visits and Sail to the Caribbean after the Med season. and back?
-Does anybody actually sail back and forth from the Med and Caribbean? each year? I suppose it takes 3 weeks each way with no guarantee of ability to work online with Starlink? Or is it better to visit the US/Lakes?

Scenario 3 -
-Please help me build these!

Unknowns
-Am I likely to get boat insurance? I have maybe 2000 miles experience.
-please help me build this out

The Wife and I once rode a bicycle for months through South America, camping. So we are familiar with roughing things a little and should hopefully have enough grit to adapt to some changes.

thank you
Rob

[SailingHarmonie]

From my experience the biggest factor in determining if someone can deal with the "liveaboard life" is if they have the mechanical chops to maintain the boat, and the attitude to actually do maintenance instead of fixing things when they break.

There is no simple answer to how much you need to know. Simple boats are simple to take care of, and much easier to deal with. Complex boats are... complex. A 45 to 50 foot cat is probably up there on the complexity scale, especially if you are looking for one with all the comforts of home.

On any boat there will be things that will hire a specialist to do/help with. If you have to hire someone to fix EVERYTHING, it becomes an expensive time sink to manage the workers and make sure things are done on time and done well. The amount of money sucked out of your wallet can be breathtaking.