@walt :
Our current boat is a Macgregor 26S. It's really great value, and you can't top it for being easy to tow and set up, for a 26 foot boat. But I know my wife isn't going to be happy, long term, without standing head room and some other amenities that the Macgregor doesn't offer.
We're in the Pacific northwest (or Pacific southwest, as I like to call it, since we're in southern BC), so lightning's not a big issue. But with the Mac, on those rare occasions when it's a risk, I lower the mast. I have my mast-raising system set up so I can do it on the water, and the mast comes down in a minute or two. Since we tow and launch a lot, I intend to set up our next boat the same way.
We don't expect to ever sail anywhere other than British Columbia, so jurisdictional issues aren't a problem. Grounding's not a big issue here, either, for the most part. Finding shallow enough water to anchor in can be a challenge, though, and, partly for that reason, I never sail anywhere without a chart. But I admit that do like the swing keel, even so, and wanted the 26S Macgregor instead of the 26D, for that reason.
Yes, I'm very happy to have this "problem!" We bought the Mac with the idea that we'd see how much we would like sailing and aim for something bigger, if we did. (And when I say "how much 'we' would like sailing" I mean "how much 'my wife' would like sailing, since I already knew what I wanted.) We're still considering non-trailerable boats because we want to do some serious cruising. But moorage cost around here is a pretty strong disincentive. The annual cost for a 30-foot slip is close to what we paid for our Macgregor!