Thoughts on new boats
Again, great advice from Double and Mitch. I''ve been very pleased, overall, with the used boat market. Its simply amazing how many well-cared for and tricked-out boats are available. My Tartan actually came with more than $3k worth of upgrades that I had planned to add to any boat I bought and those were really not reflected in the asking price. At the same Long Island broker there was an outrageous Jeanneau in the 40'' range for sale, only a few years old but many thousands off new price. Of course there are dogs out there too and your surveyor should steer you clear...things like deck delam etc. can be financially painful.
Add ons: If you are handy, consider this example. A new boat dealer installed stereo system may list for over $600, you could do it yourself, very nicely for $250.
What is really nice to either have already on a new or used boat? A list from fellow posters would likely help you. My top choices are: anchor roller, good roller furling, spare sails, good engine (old ones always seem to have a few problems but replacement is a real pain), lines run aft (particularly reefing lines), etc. etc.
What to avoid? Here too a set of items from posters would help you Jon. For example, I''m not a big fan of in-mast furlers.