I understand about wanting to fix up the boat. I remember passing little islands in the Bahamas when I was in the CG and seeing dozens of small sailboats pulled up to nameless islands. The people would spend as little as possible so they wouldn't have to work much. Seemed like a great life! I read piles of books written by live-aboards and surfed through iboats.com for months. I've dreamed of getting a sailboat and taking it to the caribbean ever since.
It's not an easy thing to do though. Cruising along on an old airhead and dreaming about sailing is nice way to spend some time too. Good luck either way!