In '85 we lost our 24' Morgan to Gloria. Friends lost a 25' Cape Dory and moved up next Spring to a Tartan 30. That summer, they loaned us their boat for a week - had to go to a family funeral. After two seasons of hemming and hawing (bigger? smaller? winnebago?), we finally bought our own Tartan 30 in the Spring of '88 - have had her ever since.
I've always wondered if it wasn't for Gloria, would we still have the Morgan 24? We sailed the Morgan for almost 10 years, both cruising and racing. We did 2 week cruises with our two sons all the way from New London to Nantucket. Every time you wanted to do something, you had to move something. During the day, all our duffels were on the bunks. When you wanted to sleep they had to go somewhere else. We accepted the boat for what it was and enjoyed it. I had raced the boat (spinnaker class) with friends and co-workers as crew, and done very well.
Moving up to the Tartan 30 was a shock. I could no longer steer in reverse by turning the engine. The main was much bigger and heavier, and more difficult to furl. The biggest plus from the change besides more room (and more displacement) was the dodger. Previously, punching to weather in a smoky SWer was survival - you got wet, the cockpit got wet, and the seats drained into the bilge. First punch to weather with the Tartan, the Admiral was sitting behind the dodger reading, enjoying the whole trip.
Move up further? Probably not. For a while I toyed with the idea of a Tartan 33 - I like fractional rigs. But not now - the Admiral's feet and ankles are getting worse and the time is soon approaching when she won't be sailing - or at least doing the sailing things she likes. She loves going to her favorite harbors, going ashore and walking around, and taking pictures. Changing to a power boat wouldn't change her desire to do those things. I think just sitting on the boat and looking at the places she used to enjoy exploring would be tough. Not sure I'd give up the floating dock and go back to my mooring, though it would be a big $$ savings. The convenience of the floating dock is really nice, and I've finally learned how to get in and out of the slip single handed. Guess that will depend on the ruling from the chanecelor of the exchequer..