I look at boat count a bit like tools: having simply one hammer in your collection will not allow you to build all the things you may want to build, you need multiple types. So I look at where I may want to go, and how many people I may want to take. Some factors are trailerability and how well they handle the water I want to be on.
18' Wellcraft 180 American - primarily lakes with family
American Sail - 14' daysailer - when it's just me & wife and I don't want the added engine noise
Canoe - exploring small places on calm water
24' Steam Launch (yet to be complete) - When I want to attract everyone on the lake and show off...
Right now it is a perfect mixture of basically all the propulsion types, so that is a nice differentiator between them.
Next boat hopefully will be one that I can dock on intercoastal water and just have ready to go whenever I want, but right now that is still a few years out.
