Re: share with me, your words of wisdom
beware a "deal" or a "steal" on an older sailboat; ask to see clear title before buying and ask about any possible liens/mortgages on the boat. Other stuff already said on this thread is good advice too. You can probably find a high 20-something boat for that price. First step after purchasing, get the boat insured and then get the gold-level Boat U.S. service; you'll need it. There will be no end to the stuff that needs fixing and that you'll want to upgrade. Prioritize based on cost, level of work/expertise required, and relation to functioning of the boat.
I lived aboard in Key West last summer for two months and depsite having only 4 1/2 feet of headroom and no on-board head or AC, I had a blast. It's a great way to live if you take to it, and it's liberating to not be tied to the land. Best of luck