... In my case, we went from one 24 sprit boat to another: The Melges 24 to the Dana 24. I would choose the Dana any day over the Melges, especially if family sailing is in the cards. You can get one within your stated budget, and your wife will be much happier with sailing in general because she will be COMFORTABLE. Don't underestimate the importance of this if you want this sailing thing to work out.
I googled the Dana, she sure is purty. Looks like a great pocket cruiser. I really like the idea of the inboard yanmar.
I've been to a few Figawi's myself (on parent's Freedom 38 named Duet). Haven't been in 3 years, wife was pregnant, decided it was getting too expensive. We usually spend mem day in Oak Bluffs now - it is practically empty as Figawi is the place to be.