First boat at 25 yo 16' Newport named the Larkspur (was a long time ago) was trailer able but I kept her the water, much easier to use, after 2 seasons moved on to a keel boat a 22' Viking by the name of Scare Crow with a full complement of inventory sailed that for 5 years then my father and sailing partner passed on to the big lake in the sky, I lost interest and donated the boat to a good cause.
Some 30 years later my wife and I purchased, last year a Hunter 41 DS, is it my dream boat not sure yet, but we love it, love spending time on weekends and extended weekends sailing the Sapphire. I forgot how much there is to sailing, how much beauty there is in the act of sailing, how much enjoyment there is in sailing, it has left me with some regret that I should have returned to the open water way sooner than I did, every time we go out now I have my father with me.