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One of the most important factors in this decision is that both agree that this is want they want to do, no matter how 'appealing' it may be to one party. If not, it will not work.
The friends and family aspect of retirement live should not be relegated to #4 or whatever on a list of 10 criteria.
I do not have any stats to back me up but I witnessed many couples move to our community in central FL (Active adult type) from the winter wonderland states that lasted less than 2 years before moving back 'home', usually because of family issues though I of course was not privy to all of their reasons.
Probably 10-15% of our community (@700 homes) were 'snowbirds' and they for the most part seemed about as happy to leave as they were to get there each year. Of course this way requires more finances than simply relocating, but it would be a good way to 'test the waters'.

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