Re: Seeking recommendations / advice
We're kind of in the same situation but our high end in price is a bit less.
Boats are very personal but for us the boats we've whittled the list down to are the Ericson 38-200, Sabre 38 and, possibly, the Moody 376. The latter is a CC and not as good a sailer as the other two, so that's something to consider.
You might be able to get a Sabre 38 MKII for a bit under $100K. Sabre is a quality built boat. Excellent joinery. Great sailing ability.
The Ericson 38-200, built by Pacific Seacraft (PSC), is in the same price range for boats built through 1993. FWIW, there's a 1998 that's listed for $144K We've seen a E34 by PSC that got us started looking into Ericson. The PSC build adds about $20K to the price but many say it's a much better build. Any Ericsons built 1991 or later are PSC built.
The Moody is not so common but there are Moodys up to 41' for less than $100K. They are said to be very comfortable but need a lot of wind to sail well.
If you want comfort but don't care about speed, especially in light air, the Cabo Rico 38 is a very nice boat. Island Packet falls into that category too but, from what I hear, is a bit slower under sail than the Cabo.