Bought my Capri 14.2 thought I'd have it forever, had it for 10 years.
Bought my Capri 22, and almost bought a capri 25 when I did... I spent all my ownership days wondering about selling the 22.
I finally bought a Capri 25, and loved that boat, put a ton of work in it, spent most of my time thinking about what I would do if I wanted to upgrade to something bigger. Wasn't sure anything bigger would work since I was on a lake that meant we had to be able to haul it ourselves and step the mast ourselves. I considered a lot of boats, Benteau 285 made the list, as did a Catalina 27 Tall. Ironically I bought an S2 7.9 mostly to prove I could be competitive with the boat the biggest winnners of our club racing used. I did well with that boat.
I was never happy with the S2, if felt boring to me. Ironic, it was a very fast boat.
I sold the S2, thinking I'd get a J27 or J92... Nothing fit it all fell through. I wound up buying a Wavelength 24, and it was probably the best setup boat I owned. Every month I owned it, even when I was winning races, I wanted somethign different... never thought I'd be able to sell it, but I knew I wanted to.
Flash forward, I own an C&C 32, I love the boat, and its what I wanted, and I bought it for as long as I am on the lake. I am tweaking it for me, but I know the resale on the C&C is good, so getting rid of it should be really easy