Hello from North Carolina while I buy my first boat

[hscrugby]

So wife and kid are on board with the idea.
I can, and do, work from anywhere. (And ~7 weeks of vacation)So that should help with bring able to cruise once we find the right boat.
We have no qualms with projects as I've done everything from rebuilding motors and transmissions to residing my house.
That said we're trying to be smart on expenses here, so we're looking at older boats in the 30-36' range. Our "long" term goal, is to be able to at least sail from NC down through the keys and depending on sea legs maybe island hopping some in the Caribbean. What we're trying to avoid is a never ending project that is a marina/yard queen.
Now history complete, we've found a few boats in our ideal price range (around 30k) that we really like. Some are just going to be too much work after we saw them, even if they look like they'd be awesome with about 2 years of hard work. [emoji16][emoji16][emoji16]
The one the wife likes is an older one that's already pulled out and up on stands. It needs the hull painted, some minor wood work (crack in the cockpit floor hatch that accesses the diesel, and some trim/polish inside the cabin) and cosmetically could have the deck painted. The issue I've got with this one, it's for sale by the boatyard brokerage guy, but to survey, we'd have to pay to move it to water, then see trial and if we like it, pay to pull out, then paint the underside, then pay to put it back in the water to sail away. The cheap in me is annoyed by that. The yard was a pretty firm answer of "no" to moving it in/out for heavy discount. The owner just lowered the price to a realistic price so he's not budging. (Yet)
Is it pretty normal if it's out of the water to have to pay to launch, pay to haul out, pay to launch?
The other boat is a little less boat 85 Sabre 32' (instead of a35') but appears turn key and is already in the water. Also a little cheaper and newer. That's my thinking, but wife has watched one too many YouTube videos saying older heavier boats are the only ones strong. Sigh. (She's not gonna join so... She's not gonna kill me)
Am I being unrealistic thinking that a 32' will be enough for weather smart cruising the Caribbean? Should I rethink my budget and save some more? Take a loan out?
Sell a kidney?
I really liked a Catalina 36 for ~50 but it sold/has an accepted offer. Should I plan to drive a lot farther then sail it back to NC instead of buying it here?
Any strong recommendations in that price range? Strong run away streaming type? (We looked at one that was in a yard and had about 2' of standing water in it. Oops.)

Thanks for any suggestions.

Chris
(HSC rugby was from playing rugby at Hampden-Sydney decades ago.)

[Adelie]

Welcome.