Awesome topic. Thanks for posting the question and also thanks to those who responded.

My wife and I are in a similar situation. But reversed. OK, mostly similar, but we're already in Florida.

We're in the process of retiring, and so tired of the Florida summer heat. We're looking to spend our summers back in cooler climes. Great Lakes were first to come to mind (we're from there) but New England is certainly on the table. Loved hanging out in Traverse City. Always hoped to get an opportunity to sail there.

Downsized boats 20 years ago being too busy to spend much time on the boat and living too far inland. Going to upsize again. Figured we buy up north rather than spend the whole season just getting there.