If he’s military contact his chain of command, because he sounds like a real pain I’ve had to counsel my soldiers and help them pay bills before.

However, it's a pain to receive the bill and then charge the tenant for that amount.

(Side note, my income has been kind of crazy & all over the place, so seeking pre-approval for loans has been a pain.

In full transparency, he can be a pain to work with and I haven't sent anyone to him in a few years because I don't know anyone buying in Atlanta right now.

They are the patient and you can’t possibly treat their symptoms or make the pain go away without asking questions.

I'm not a huge fan of the psychological impact of this as you get a big lump of money and it tends to make us feel 'we need to invest this ASAP' - which isn't optimal IMO.The above I'm told will often work under the traditional 'retail' arm of most banks. 

There are dues you pay to get wiser, some are more painful than others. 

The tenant has been a pain to deal with on other issues and I'm pretty sure he does not want the inspection to happen as he knows he will be responsible for the repair.

That allows me to "talk shop" with my investors so I can be able to empathize with them on any of their pain points.

Be a slight pain in the rear, without being too big of a pain.