I've got a MacGregor 36 (have had it for about 7 years). It's a great boat but generally, we put it in a the beginning of the summer and take it out at the end (we don't trailer it around). It's quite
a bit more work to set-up and take down than a Stiletto but has a lot more room in the hulls too. In September, I sailed it to Wisconsin and made 60 miles in 5 hours in fairly large seas (5-10ft waves) and not much sail up. Portions of
the trip were spent over 17 knots trying to keep the bows from tunnelling into the waves in front of us! The boat is a real joy to sail. She sails nice and flat (18ft beam is great) even in big waves and screams along. The acceleration of
the boat is unlike anything a mono-hull sailor ever sees unless they're sailing over a waterfall! The other thing I really like about it is it's simple rigging and designed in safety. The mast is full of foam and won't
turtle easily. There's redundancy in the rigging/stays and it never feels skittish, even in water I wouldn't feel comfortable in, in a 40ft monohull. The only bad part of boat is that I've got to sell it.
as my partner wants out and wants to defect to the dark side (a big fat, clumsy, slloooowwww, heeling mono-hull) and I've just launched a new family which keeps me from buying him out. Let me know if you want to add a bigger boat to your fleet! It's a fresh water only boat and is in very good shape!