Dream of Sailing as a living
jeff makes some great points. i highly suggest that you get the book, "The Cruising handbook''" by Nigel Calder. he has a wonderful discussion about what to look for in a good cruising boat, complete with checklists to take with you when looking at boats. We found this book invaluable when we were first starting our boat search. it also has lots and lots about cruising, navigation, boat systems, etc. A GREAT book.
You might also want to read the classics like "Desirable and Undesirable characteristics of Offshore Yachts". I have a stack of good books to suggest to you but they are all at home, where i am not right now. Send me an email and I''ll give you titles and authors: email@example.com