A few points (a few made, a few not):
-IMHO, a boat over 30' would be too large for you. The sailing part would be OK, but docking, anchoring, reefing, etc. can all be 'challenging' and the bigger the boat, the more effort, skill, practice, etc. required.
-There is no way I would spend even close to 60K on a 'first' boat. You don't know if you will like sailing, or what kind of boat you want, or what size boat, etc. There are lots and lots of very nice boats available for around $20K. IMHO, you should start at that price. Then if you love sailing you can easily move up. If you don't like sailing, it will be easier to get out.
How many people will be sailing with you? How many people would over night with you? In all likely hood, a 25-30' boat would be more than sufficient. Once you get to the 27' and larger size you get all the important amenities - diesel inboard power, pressure hot and cold domestic water with shower, galley with propane stove, real marine head, comfortable berths, etc. A 27-30' boat would be perfect for 2 people and acceptable for 4 people. More than 4, or for longer than a week would require a bigger boat.
There are lots and lots of 27-30 boats available. Catalina, Hunter, O'day, Pearson, Newport, Tartan, Sabre, etc would all meet your needs.
Curragh, 1986 O'day 35
Mt. Sinai, NY