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

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. 

(I know it would be a legal disaster if the property goes to foreclosure and the person he sold it to, loses the house and of course sues the borrower for being stupid).

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.

I don't know a single person who regrets starting out with a quad and house hacking.

I get a lot of requests for people who want to hold a wedding at our houses.

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.

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.  

You can get houses at huge discounts and it is a great time to buy for appreciation.

Like any city, there is dilapidated housing stock in rough areas that can cost more to upgrade than they are worth.