Welcome to the Forum, Joe! We're glad you've joined us.
I was born and grew up in Colorado, myself. I also had a condo in Kihei at one time - now my ex-wife has one.
So your post caught my eye.
It sounds like an interesting proposal to me. The only problem I see is that if someone lives where the winter is cold and snowy, and they have a catamaran
down in the Caribbean
, why would they choose to spend time on land in Hawai'i rather than sail their cat? Someone might, though, if they just have to get out of the snow and their cat isn't available.
Good luck to you in finding the right person / situation - it only takes one!