Posting all that in a public forum is a real swell idea.  

The market then crashed in 2007 and when I was forced to PCS, I was left with a house that was worth way less than I bought it for and I couldn't rent the home for what I paid every month in a mortgage, so I was left with a house that was underwater and was bleeding cash every month.

Stop the bleeding.

Again, paying $100 o whatever for every time the tenant see a roach or a mouse, is dumb in the long run....again, your PM should know that....Some or all of these could be legit....but when there is a pattern, you need to get to the source of the pattern and stop the bleeding, not put a band aid over it.

Hire a professional and get it done right and as quickly as possible.Consider hiring a property manager to stop the bleeding.

Now it has swelled to what, 35 people or so Shawn? 

Personally I would stop the bleeding and tell them they either need to catch up or move out. 

Don't come off as a corporate stooge who wants to bleed them dry.

#s may look good today, but you might bleed out slowly next 5-10 years.Something to consider depending on your life situation (e.g. busy professional/w2 worker who may find better returns climbing up the corporate ladder while creating this on the side).

DO NOT, I repeat DO NOT let them stay hoping you can get the back rent, it is gone, you can only stop the bleeding going forward.