First Time Sailboat Buyer, with the Intention to Live Aboard (Tampa Bay Area)

[Cacique]

I'm all for your boat acquisition but trust me DON'T buy a wooden boat!!!
go for a grp (fibreglass).
But living aboard has to be much cheaper than a house, especially as you have the DIY skills, but be aware boats need quite a lot of work and everything is marine quality so screws for a job on your house may be $5 but on your boat will be $15 but overall go for it.
I know you have little experience but you are aware of this so if you are willing to take it on, go for it, you can learn as you go and have already found this site which can help you greatly, just be aware there are many people who will say "I wouldn't do that it'll go wrong, cost too much etc"
Unless the boat sinks you'll be able to sell it for something (Unless you completely ruin it) and hopefully you'll have insurance so even if it sinks you'll get your money.
I wish you the best of luck, go for it, if you don't you'll always wonder what if I'd bought that boat.

[The Smokester]

I think you can live more cheaply on a boat in the marina than an apartment or house on land (cash flow-wise).

Just remember that even a fiberglass sail boat is more complicated than a small village. Mine has two sewer systems, two electrical systems, three or so water systems, two motive power systems...and, you got to keep most of them working well in a corrosive environment or the darn thing might sink.