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There is always going to be some thing or other that detracts from the decision to move to even the "best" place. I recommend a spreadsheet with maybe five locations and 12 criteria in order of priority. Stack up the points for each location. Mine looks somewhat like this:
Landscape/topography pref
Climate pref
Housing price range
Safe* from natural/manmade disaster
Ease of transportation/travel
Hours from grandkids
Medical
Health insurance
Senior services
Access to quality food & services
Political feel
Recreation (our kind)
I have some friends who retired recently. They had five cities in five different states that they were considering. Over the course of two years pre-retirement, they visited each city for one week. They did "touristy" things in the region, but they also acted as though they were locals - went grocery shopping, went clothes shopping, went to local cafes, tested drive times for going to hospital/doctor appointments, looked at the real estate market (toured a few homes in their price range in each city).
Slowly but surely they whittled down their list to two cities. They visited each city again, doing a deeper dive into what it would be like to live there (getting around during rush hour, how much development was taking place). They also began seriously crunching the numbers of exactly what the pros and cons were to each city they liked.
One stood out by a landslide, and they promptly moved to NW Arkansas once they retired.
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