Never let others make you feel guilty for having strong finances.

You should not feel guilty and neither should a provider.  

I feel that I will have to end his month to month lease if I want it treated and feel guilty to do so to an elderly tenant.

Since you bring up the Qatar citizen living in Illinois who was arrested on charges of being part of an Al Qaeda sleeper cell - he pled guilty didn't he?

You'll have to go to a public hearing and plead your case for your units to be restored.

Don't feel guilty about that.

You are absolutely presumed guilty until proven innocent and don't even think about getting discovery.  

I sometimes feel quite guilty about the career/life choices I made in college to not take that route now, as it seems that working for a year or two for a large paycheck could really be advantage for funding real estate investment.

Here is the thought process: without a letter you are trusting an agent, that doesn't know you, to plead your case.

By the attorney general standards I was guilty until I could prove myself innocent. 6 months later all was cleared (case dropped) and done with no issue, not fun but educational.I have no desire to even touch who and what is a couple, married, unmarried or whatever!