So, I finally tracked down a boat. I've spent about a month touring the coast of Florida by car, hitting marinas and looking into local boat sales classifieds and brokers. After rounding through the Everglades and up through Miami and Ft. Lauderdale, I stumbled onto and advertisement for a J/24' in Melbourne, FL. I drove up and took a look. Took a sail, and closed the sale. I'm now the timid owner of a small racing sailboat.
After looking at around 20 boats, I settled on this one because motel and driving costs were really starting to add up, as were inexpensive nights of sleeping in the cramped back seat of a saturn. The J/24 isn't meant for crusing, but it has enough space to live in, especially if you don't plan on standing up while inside. It is a firm boat and I got it for a reasonable price. After some repairs, I think I'll be able to sell it for a little more, and move on to a cruising boat that will fit a live-aboard better and be able to get me up to NYC.
I've moved the boat from the prior owner's slip over to a new marina where I'm living in Indian Head Harbor. It's the cheapest rent I've paid in years, and it's cheaper than even weekly motel rent. I'll be living here until at least the end of March; doing repairs and learning to be comfortable single handing a sailboat.
I went out yesterday for my first solo sail, and... well, it will get easier. I'm still very anxious about and while docking, but in fair weather I feel safe on the open river. When coming back into the slip yesterday, I failed to slow down enough and really bonked the bow into the dock. I thought I had slowed enough. The outboard motor I have has no reverse so must be spun around to power aft, and I just timed things wrong. Need more practice. Much more.
In any case, I'm still alive, in case you were wondering.