OK, this sounds like a silly question but I really want to know if this is necessary and why.

This may sound on the surface as if they are being shifty, but I don't think that's the case.

If you’ve put the money down for your son’s house purchase, make sure he’s agreed to some amount of “effective” rent so he’s incentivized to collect from everyone else so his share of profits makes his living cost closer to $0.

As it sounds like you may be familiar with both Flips and Buy & Hold - why don't you let the market make the decision.

You did make a good appointment that can effect the cost related to the age of the building.I just saw that the age of the building was included and I would see if there are any extra testing or repair costs associated with that age. 

It sounds like you have a problem tenant on your hand.

Sounds like delegating the rehab and management was really successful for you.

Sounds like you'll be in a pickle when you move if you don't sell it because you'll be feeding the monthly mortgage payments to make up the difference between what you collect in rent and what your mortgage is.

@Kevin O'Brien sound like you have some money and a good work ethic.

In your case, it sounds like the CO may be trying to help you out, but trust me, his/her real concern is for the service member, and keeping him/her out of financial trouble.