Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Now he uses property managers and I would bet dollars to donuts those professionals aren't offering cash for keys.I have 15 years experience managing 400 rentals and I have never offered cash for keys.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

80% of professionally managed properties in my area are at market rent but under potential rent.

See Real Estate Professional under Activities That Aren’t Passive Activities, later.

You should not do anything to keep her, she is a bad tenant and a professional tenant.

Does this person have any professional licenses?

if there aren't any identical comps, or if they're 120, 140, 162, then you need professional assistance on determining it.you also have to factor in ALL your costs. 

Looking for a professional opinion. 

I’m trying to have him see the bigger picture if he puts money in tax advantage accounts first and strategically uses a tax professional, that he will be able to offset his high tax bracket w2.