Steve, I cannot imagine living on board full time. And I would think it might be tight for that.
Are you someone that does most of the work yourself? The yards in CT are pretty expensive. I am hoping that there is not as much mechanically that goes wrong. Have you had any repairs since you bought the boat.
Also do you have the main sheet furled in the mast or the lazy jacks. I haven't found a boat that has every option we wanted and it may come between choosing between the furled main and a bow thruster. I was concerned that the lazy jacks aren't quite as easy as the furled main. Although a sailor told me just sail with the jib and forget about it entirely.