More on H23
Kevin, I have to say that based on your stated requirements, you may not want a boat as small as a 23' anything. Regarding the h23, I am the orginal owner of a 1986 h23. Obviously I like it, a lot. But I also understand that like any boat, it is the product of a series of compromises. I am not bothered by the low overhead - I've been in shorter cabins, and I like the reduced windage it provides. I love the size of the cockpit, but that reduces the available interior volume. Because I'm an inland sailor, the ability to trailer it easily has been great. But trailering limits the size, including interior space, of a boat. There are some who claim the h23 is "tender." I disagree - noting that one of my kids favorite sailing games was to sit on the lee rail while I pulled in the main to make her heel as much as possible. Speaking of kids, we raised three, with many a sailing weekend. Sleeping was kind of like being in a tent - the two girls in the v-berth, son in the quarter-berth and my wife and I in the midships "berth." But everyone had a place to sleep comfortably, and the galley was adequate, but it would not be acceptable in my house. As for performance, go look at the PHRF (performance handicapped racing fleet) ratings of the boats you have in mind. I think you'll find the h23 has a decent turn of speed. In summation, it has been, and still is, a great boat for me. But not necessarily for you.
Frankly, the various discussions of the "perfect boat" are somewhere between BS and hot air. Perfect for what and for whom? There is no such thing as a single "perfect boat." The question comes down to whether it will do the things you want it to, including those things that require mutually antagonistic traits, and how do you feel about being aboard and under sail on that boat. The suggestion that you slow down on putting your money down and take time to sail on as many different boat as you can over the next several months is on the money. You will be happier, and maybe even save on your purchase price, if you take a little time.
Good luck and happy sailing.
Jim Kolstoe, h23 Kara's Boo