I have never downsized from anything; I bought my M15 when I was sailing quite often on someone's Clipper Marine 26, though. One huge difference was that when they took the Clipper Marine out of the water, it never went back in. It sat in their driveway for years. My M15 sat in my garage for a few years, but was pretty much ready to sail again when I wanted to sail it. When I bought my M15 I expected to do more cruising but I really never have. Mostly it has been used for day sailing. But I still enjoy the cabin being there. It provides dry storage for things, it is a place for privacy when needed, and a place for a guest who decides it is getting too rough or too wet in the cockpit. When I sailed with Labradors, they liked to ride in the cabin. In some ways an M15 is overkill for day-sailing, but it is so easy to step the mast and get it going that in other ways it beats many smaller boats. Even with the small cabin on the M15, you can send extra passengers in there when you need space to work (at least, it worked with my kids!) I have to admit that in many ways I prefer single-handing- no one to get in the way- but its fun to have company, too. I do notice significant loss of speed when I have several extra adults in the cockpit. While on the topic of trailer-sailing to many destinations, you have the added advantage of being able to sleep in your M15 or M17 at a campground on the way to where you are going. Bobbie