was going to leave a comment here, but....
While I admire the dream and the plan, I'm wondering a bit about you choice of boats. Some of them are blue water capable, many are not, and none would be without extensive repair (read costly and time consuming) given the boat bucks you have.
All of them are wonderful, don't get me wrong, but on your budget, the repairlist and cash needed for ANY boat of that type will shake, shock and awe you into submission and possible flaming of your dream.
I'm not trying to pee in your post toasties. really. but you're not the first with the same type of dream.
I'm here to tell ya, that unless you're SKILLED in FRP repair, epoxy, rigging, engine mechanicals, not to mention woodworking, glazing, plumbing (bucket is not really an option, don't go there) & electrical to start, this will be a futile effort. You think med school is hard? Diagnose why flipping on the anchor light just caused your battery to become a vicim of smoke technology. (it worked till I saw the smoke)
I'm not talking about reading a book and following pages. You need to be able to actually lay up 'glass a couple of times to do it (notice I didn't say "do it good" ).
Might I suggest that instead of looking for a hole that holds water (and thats what you'll get based on your budget and boat choices) that you take a moment to consider one of the thousands of "sailable right now" production boats.
Examples, Catalina, Cherubini designed Hunters, & O'Days, just to mention a few.
Many of these can be bought for 5K to 7K and you can sail them away today , WITHOUT having to replace a motor & sails today & not have to worry if the mast is going to fall over on you.
None of the above is bluewater capable. Yes, people have done it. blah, blah, blah. I'm not going to, and I'd wonder about the sanity of your spouse if she's going along with that plan on any of those boats.
They can be nice coastal cruisers. But then again, I wouldn't trust a rebuilt boat by someone with no experience on anything larger than a farm pond anyway.
I think you'll find that even if you DO continue on your plan, within a couple of years you'll be suffering from "threefootitus" and looking for a more suitable watercraft anyway.
We are not primarily on earth to see through one another, but to see one another through
Some people are like slinkies: not really good for anything... but you can't help laughing when you push them down the stairs