Yep, I did the same thing....
I moved up from my 1984 31 to a 1993 37.5, love the 37.5 but still long for my 31. I wanted the additional room (head, aft cabin), enhanced galley (full stove, refer), a/c/heat, etc. I had been cosindering adding a bigger stove, etc. to my 31 but I felt that adding $$$ to my 31 would not pay off in the end.I love the 37.5, it's a very fast boat and easy to sail. The added room is great. Having a larger engine is the best for me because I have to motor out 2 rivers to get to the bay.But, it's a lot more boat so everything is more. Slip rental is more, and it takes more effort sail it just 'cause it's bigger. And, with all the additional bells and whistles there is increased maintenance and $$$. In the past year I had to rebuild the transmission, replace the refrig, water pump, and head, plus buy the new toys I wanted. (Still want a windlass which is really a necessity on this boat unless you are in great shape.) The surveyor did not necessarily point out these things, but he did a superb job. My boat had not been used for a while when I bought it so it stands to reason things would break.Bottom line, I got a great deal on my 37.5 so I'm not sorry that I did it. If I had paid top dollar I'd be less happy.I still miss my 31. It was easy to sail, easy to maintain and I did not worry so much. Most importantly, it was PAID for.I think it really comes down to how much you will/can use the boat. When I reviewed my 2001 finances and saw how much $$$ I spent on the new boat I was stunned. And 2001 turned out to be one of my busiest years ever at work, so between repairs and work, I did not use the boat as much as I planned. But who does? It ain't a cheap hobby.But then again, I'm in love with the new 466. Just call me an idiot!Email me directly if you have other questions dcdon@hotmail.com.Good luck.(And note, Steve Dion is very loyal to the 31, but he secretly wants my 37.5!)