"Good about deductions" sounds a lot like "doesn't make enough money to be a homeowner", so he should keep renting from someone else, and you should do what you're going to do with the money and wisdom you earned.Of course I don't know your son, but I think this is too dicey and you are too close to the situation.  

It also sets the expectation that rent should be paid through the system you’ve chosen without escalating the situation.

The PM should be an expert on state law, and they should have policies and procedures in place to handle these situations.

Not sure your living situation but something I would definitely consider if possible. 

Not knowing your situation, you may or may not benefit from a cost segregation study. 

I’d simply ask in what situations where the broker and the brokers firm did nothing to facilitate the sale do you think you should get paid a commission?

The only time we will not make an offer site unseen is if we run into a situation where an owner or a realtor won't accept site unseen offers. 

Obviously tough to give advice based on minimal info and no info on your personal situation.

You'll have tenants that don't pay, damages made, and potentially other disasterous situations occur on your properties. 

If it is, explain your situation and ask to file a complaint.