I would consider a condo in a ski resort. This would give you rental income in their “season” and allow you to use this property in the summer. We own one with ski in/out access, heated boot room/ski lockers, etc in the winter. In summer there is a golf course, gym/spa, pool, mountain biking, etc and nearby hiking, fishing, farms and charming small towns to explore. Those in VT would probability rent best in season. Alternatively I would consider a NE beach destination such as Cape Cod or the Delmarva peninsula in DE. They are building lots of new senior communities in that area of DE.
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