That's the classic dilemma - trying to please the head and the heart. I'm looking for that "last boat" (wishful thinking) that does both. We're downsizing so budget is not a major factor as long as it's not 6 figures.
@captjohn, that's exactly where I am now. Through the years we've had everything from a Grady White 22 up through a Bertram 36, all of which we've had for a few years before moving on. All have been great in one way but lacking in others. Currently we have a Hunt Harrier 25 where the issue is ongoing maintenance needs. If it were just a little less work we'd keep this boat forever. Between the brightwork and the stern drive it's just a little more than I'm looking for. That, plus ongoing hauling and storage fees which really start to add up after a while. Thus, we want something we can haul and store ourselves.
To take a crack at my requirements:
-Outboard engine
-20+ kt cruise in flat seas
-Can make it to the Vineyard (and back) on a good day with margins for weather and fuel (that means ~100 mile range)
-Comfortably trailerable without getting a new car (puts boat weight <3000 lb, length likely in the high teens)
-Minimal, reliable systems - no head, no plumbing, fewer things that can break
-Quality finish with good materials and no exposed brightwork - but I love brightwork when it can be protected from the elements when putting the boat away
-The hardest requirement: that classic, timeless look that you just want to keep looking at on the mooring or in the driveway.
I'm in the "know it when I see it" camp, but if it doesn't meet the basic requirements then it's a no-go. I've spent hours and hours on the classifieds and yachtworld, etc but I still don't think I've found "the one" quite yet.
That Tripp 22 is right in line with what I'm looking for. Good recommendation. I'll look around to see if I can find one that makes sense.
I'm also looking for names of other smaller, less well known makes to see if any of them could work.
I could also see going semi-custom with a reputable boatbuilder and proven hull design. I'm also not opposed to getting a high-quality older boat to repower, upgrade or modify if it's worth it.