You sound like a good candidate for the Sailnet Singles Scene...Pirate's Booty keeps bugging me to start one!
As for the boat, I would recommend you get the biggest boat you think you can comfortably sail. A 35 footer for example will give you significant advantages in space and sailability over a 30 footer for example. However, that being said, I really like the Island Packet 30 for a liveaboard. I believe you can find one in the 50-60K range. They are solid and well designed boats. Plus, they hold their value...