If you don't/won't have WiFi then you should either consider a SimpliSafe system that you can move around from house to house, or some type of Trail cameras like hunters use for identifying game areas.

We all assume this isn’t a house you’d buy with your own money.

I currently have a 4/2 SFH/LTR/Section 8 house under contract and I am getting quotes for property insurance.

Free healthcare free cell phones free housing.  

Lots of older houses but there seem to be several that have the potential for cash flow and while not exactly modern on the outside, have been renovated inside. 

This is an obvious fair housing law violation because you are choosing which prospect get the concession.

Rents have been pretty close to what the housing authorities advertise, sometimes even a bit higher.Fort Wayne’s a solid spot with low taxes and good cash flow—definitely worth looking into.

(Previous rent was $1,300 but we're about to put in a brand new kitchen from the studs, new flooring throughout the house, new furance, adding A/C, etc).So do we just pay for it all upfront and mostly drain all of our savings, or do I let the rent pay for it and utilize our other savings to get a second property this spring/summer to increase our cashflow? 

He'll still be renting - just from you instead of others, and at all the costs to you that you have enumerated.Your son doesn't "need" to buy a house.  

It seems to me that they all whether paid of free, will all have the same exact amount of houses because all the transactions are all public and so they seem to compete with each other based on the quality of the data of the houses, how up to date it is, and the user experience in configuring the how the layout is.