Flipping in small towns

[Michael Rosenbaum]

I am a new investor and am looking at areas for my first flip.  My fiancé and I are digital nomads and will eventually want to settle down and start investing in wherever that place is.  In the meantime we want to get started by flipping a couple of houses close to where our home base is.  There is a town about 2 hours from our home base that is very small (around 5,000) and generally run down.  My father and his business partners are from the area and have been working for the past few years on rejuvenating the area by investing in businesses like a small hotel (which is constantly at full vacancy), restaurants, coffee shops, a UPS store, a small construction company, a dance studio etc.  There are some big tech companies that are building and planning to build some microchip factories in the near future that would be within driving distance of this town. 

All that being said I like the idea of this town as a stepping stone into the flipping game especially because of the very low upfront costs based on the prices of some of these homes that need a face lift.  There is also the prospect of using my father's construction company as the contractor to help with the renovation.

I am eager to learn what experienced investors in this forum think about investing in a tiny town like the one described above.