A Different Approach to Snowbirding

I've wondered about this as well- how to get Urban amenities and a home base, without high overhead. I think finding a small house in a small town would be easiest, based on most of your requirements. My friend for example has a smaller house in Lebanon IN -and says he has everything he needs in town, everything he wants in Indianapolis 20 minutes away, and everything he can imagine in (or connecting through) Chicago, 3 hours away. I'm curious what others suggest.