I know what you mean seeing the boarded up / empty locations on Main St in many of these towns. We just completed a 16 day ride from MA to Jacksonville FL to Fort Scott KS and saw alot of this. Even the large places, brand new car dealer buildings empty. Houses abandonned and and falling down. However the bright side of this is the ride to places you would not normally go to. We did 4 different tours this trip, Hard to keep track of which flag do we pull out .