If my health remains, that is. I know so much more about how to get the most out of it than I did in my 30's, 40's and even 50's.
I don't think a happy sailing life is an easy thing, it takes some knack and experience.
A neighbor just sold his lobsteryacht and bought a Morris Justine 36. Always a sailor in his younger years, he got tired of the powerboat. He looked into Daysailors first. I think he came to the same conclusion I have.
This in not a particularly good coastal area for day sailing. There's a bit too much distance to travel to fully enjoy sailing here. I think you need enough boat to take advantage of it.