Since I am in realist mode, I here are two things I have noticed watching the retired and/or elderly:

1. In a town without very good public transportation, when you can no longer drive, your world collapses in. Getting to grocery stores and medical appoinments gets to be an ordeal. Having great theater and resturants and a bus system that shuts down at 6:00 PM is not all that different from not having great theater or restaurants. The lsit goes on and on.
2. Gentlemen, when you die, the chance that your wife is going to move closer to the kid(s) is somewhere between 100% and 110%. That's a low estimate.

Those two factors explain about 95% of the empty dream houses my parents use to point out to me when we drove around New Bern. "There's the Jones's house. He has 1600 sq foot workshop, he was quite a woodworker. When he couldn't drive anymore, they had to move back up north. That's the Smith's house - they loved that boat. She took quite a loss when she had to sell it after he passed. I think their house has been on the market for 3 years, ever since she moved back to Connecticut to b closer to he daughter..."

My big hope is that at least one of my kids is living in a college town when we are retired - from what I can tell, the only public transportation systems that run after dark in non-metropolitan areas in the US are in college towns.

One other dismal note - a big part of the medical question has to do with auxiliary services. There are a number of towns in my home state where the local hospital is top notch, but the available medical rehab facilities look like something out of a Dickensian pauper's prison. If you can, try to investigate all tiers of health service!