I can see your line of thinking. I'm a sailor who now has a C-Dory 22 (lots of sailors here, you'll find). There are many things I like about the boat, but just to mention a few:
(And of course there are a number of boats that could do these things.)
This is a bit of a ramble, but maybe still interesting.
I can totally adjust the experience to my energy level, time, interest, etc. What I mean is that because it's on a trailer, I can transport it where and when I want. I can store it indoors, which really cuts down on maintenance. I can use it a lot, or I can leave it happily stored while I do other things, guilt-free. Sure, it's a boat and so it needs things, but it's not like a boat in a slip that if you're not keeping up on it is basically deteriorating by the minute. (Of course there are wonderful things about boats in slips, but I'm simply speaking from the other angle.)
There are enough projects (or potential customizations) to keep even the most devoted putterer happy and busy - and yet the boat can be used and enjoyed without doing any of that, if one prefers.
It sounds like you may not be planning on trailering (and trailers and trailering are a complication, although one many of us happily put up with), but if you do, there are a bunch of neat places you can go: Lake Powell, inland rivers and lakes, distant cruising such as the Inside Passage (distant from where you are anyway). These are all fun places that I either couldn't do on previous non-trailerable sailboats, or which I could get to but it took considerable time/effort.
The on-water experience can likewise be "adjusted" to suit. Feeling tired, gimpy, or just needing to relax? Then you can just motor (in enclosed comfort) to an anchorage or dock and relax. Miss sailing? I spent some time boating in tandem with a couple who had a Snark type sailboat along on their 22, and using it at the anchorages brought back all the fun parts of sailing a light boat, many of which I missed on a larger sailboat. Or, explore the nearby surroundings in a kayak or a powered dinghy, hike, swim, etc. as the mood strikes you.
As mentioned above, many of these things can also be done in other boats, some with a bit more luxury. Everyone has their own place on that scale (or chooses a particular place for a mission). The C-Dory 22 is a bit like a Volkswagen bus. By that I mean, does it "all" in a compact, multi-use space. Not the most luxurious, but sturdy and simple. Not super luxo, but has personality and gets thumbs ups. That kind of thing.
For me the 22 is right below the "tipping point" on a number of things:
1) I can tow it with a number of different vehicles, and being able to keep it near the 5,000# all-up range means I don't need to get into the next tier of tow rigs (I tow with a van/RV so this is key).
2) I can mentally afford to hang onto it even if I'm not using it 24/7/365. I don't know exactly where that "line" is, but I know I wouldn't feel the same with, say, a $50k+ boat. Different for everyone of course.
3) Since I can store it indoors (or alternatively under a fitted cover), I can leave it while I do other things and have it stay reasonably "the same." That didn't work with a slipped boat.
4) Simple systems are easy to winterize, etc.
5) And yet if I want to tart it up a bit, there is lots I can do.
Who knows what will end up being right for you, but I'm envying you being able to go meet srbaum and see his boat(s). He is a true boater and extremely knowledgeable. He has generously extended similar invitations to many of us, but I'm much too far away at the moment to take him up on it. You're practically next door :thup
Have fun with it all
Sunbeam