Like the city. Great in winter.
Oh yeah. My daughter (UConn '10), grandkids and good guy son in law live here.
A way out idea would be Galveston. It's not glamorous. The Jersey Shore of TX. You will KNOW you're not in Connecticut anymore. People live there year round. Gulf front...have to try hard to spend 450K. That's sand in toes beach/water front. 1 hour to Houston to get your big city sports, art scene, way underrated food scene. People are friendly.
Transfer residence to TX and there is NO state income tax...and I could use Husky mates for the Tuesday night games as there really aren't any even casual fans here.
Chicago retirees go west coast, NYC and Boston to east FL coast. I like the desert as a visiting spot. Personally wouldn't do 5 months there.
If you care, as with FL and AZ, you are never more than DeChambeau drive away from golf. 12 months open.