Thanks so much. You guys are awesome! I have my work cut out for me on many levels, and I have to be wary of my tendency to be impulsive too... Irwin, Gulfstar, and Hardin are turning out to be the most "bang for the buck" so far - with regards to length/strength/accomodations/amenities in my budget range.
I met an owner of a 50' Gulfstar who showed me a little bit about looking for soft spots, etc and it was very helpful. As I make progress, I'll keep posting until I find something good. I don't think I'll do any serious looking until October - and, as a bonus, maybe the prices will drop even more as we head into winter up here in Boston?