I too am not far off from ‘retirement’ and this topic is subject to regular conversation with my wife.
I have extensive family in FL and own property as well, but won’t go as far as moving for a lot of the reasons that’s been stated.
For me, it’ll be where ever my kids eventually settle as that’s most important to us, being near family and loved ones. My oldest is considering schools on both coasts, and nothing in the middle part of the country. I live in Maryland which is a high cost state and is not conducive for retirement. Property taxes are insanely high and quality of life is not as good given proximity to DC. With property values reaching NYC & SF levels, It will allow me to have good flexibility to relocate.
I have considered moving back to Austria, but would be there alone with no friends or family.
One thing is for sure, climate and access to a good watchmaker is a definite driver in my decision.