Hey Devil Dog listen up: get the most boat you can afford, period. The second law of thermodynamics means you lose everytime you upgrade, don't think about it like real estate (unless your callsign is 'slick').
My first boat was a 45' Morgan and I'm still very happy with her. I recently thanked the fellow Marine who told me ten years ago: 'get the most boat you can afford.'
There are always a good number of boats around Oriental (where we have a slip). Currently probably 10-20 boats in your price/size range (even a $30k Tiburon with no standing or running rigging, speaking of your project boat). If you search NC in yachtworld you'll ge a good feel.