The tenants are all lovely people, though they seem to be concerned about 1) the condition of the garage, 2) the fact that the windows all let in cold air (by the look of them, they're probably as old as the building) and 3) the lack of landlord response to their multiple other (small) concerns about the property.

If you do choose the REI route, if a crash happens have your son take a couple roommates for $400/month, Air BNB it for the summers when school is out, put up solar panels, figure something out. 

ive seen a few on air bnd and if done right it seems to be a money maker .

If you want him to do the work hire him, with a well defined contract as you would any contractor.

What if you have a property management hired?

Though be sure to thoroughly vet any new agent before hiring them or signing an exclusive agreement.

You hire a great lawyer that is in the business.

The increased/inflated supply of money leads to larger/higher prices - sort of like how increased air in a balloon leads to a larger balloons - as people can "afford" to borrow and therefore "afford" to pay more.On the other hand, there's not much money at all available to borrow to rent! 

Trying to avoid neighborhoods that would require me to hire security for a property, but I don't mind taking some risk.

I am not a cpa, but I hire one to do my income taxes.