Having built 2 MiniCup 12' sailboats (and rebuilt them)
Built a 9' nesting 2-Paw dinghy
Built a 20' Tolman
and owning a canoe, kayak, and sailboard and a 28' S2 sailboat, you
might think 8 boats is enough. Of course I also built a slide-in
truck camper this past year too.

So, what to build next? A bigger sailboat? I really like my 28' S2
with her 3'10" draft and 13 hp diesel. However, I am intrigued by
water ballasted boats like Michalak's Cormorant due to their
trailerability.
Another possibility is the "Diesel Duck" motor sailor because she
offers serious long distance cruising but at age 53, I may be beyond
that time of my life and more into other things.

A bigger Tolman? Maybe just to have the cabin and better sea ability
but my 20' sure is easy to trailer and launch. My 20' takes me 90% of
the places I want to go and would take me to 95% if I was to take
risks (Key West to Dry Tortugas). I might just give her an interior
deck and big scuppers but her small deadrise would never allow her to
be a good sea boat.

I suspect that as I get older, long distance cruising under sail will
be less interesting to me and shorter trips for snorkelling etc will
make more sense meaning a power boat.

Maybe I should not build any more boats, I dunno. However, building
was fun