Well, you have definitely defined the best reasons for having a trailerable boat! You've made the case for it very well based on the beautiful locations that you have enjoyed. I think the matter comes down to how you want your sailing to evolve. Obviously, you don't have a fixed routine that has gotten old. But I do suggest that age makes a difference in how you enjoy your life. I wonder if the physical demand of setting up and tearing down is wearing thin ... it's understandable. Instead of always looking for new destinations, perhaps think about enjoying a favorite location with more emphasis on being settled. It's a change of attitude for sure. I've been through so many changes in my life, that I don't often think twice about what I miss from the past.@Scott T-Bird
yes, you nailed it. Our favorite sailing destination is grand traverse bay. We’ve sailed out of Sutton’s Bay, and Northport, and Elk Rapids.
We’ve also trailered to Escanaba, DeTour Village, and dipped our keel into Lake Superior out of Lance (or Barraga - I can’t remember). We stick to bays on our small boat, all of those places have nice bays to sail.
I've considered Muskegon. We sailed our old boat on Muskegon Lake a few times, I think that’s 2 1/2 or 3 hours away. I’ll have to check into some of the other Lake Michigan towns. I see myself, especially in the first few seasons of getting used to the boat, sticking to bays. Lake Michigan towns tend to be a little exposed to high waves and big water. I still have a small boat mentality - I’ve got plenty of respect for Lake Michigan.
With a larger boat, you definitely will change your mentality. Your respect for the challenging conditions on Lake Michigan is certainly understandable, but I suspect that with your experience, you would have no problem adapting and enjoying the new challenges. One of the great things about putting your larger boat anywhere on any of the Great Lakes is your ability to sail to a new favorite location!