Well, I bought my Coronado 25 knowing that it was a training boat that I would only keep until I had a handle on sailing. It was cheap, tough, simple and forgiving. It didn't go to windward very well at all.It doesn't take long for ten foot-itis to set in with new-to-boating owners.
I intended my Pearson 30 to be my final boat. My wife, not I, decided that it lacked sufficient storage and amenities. She chose the Tartan 33. She is still happy with it so I'm still happy with it. Unless we win some kind of lottery, this is the last boat.