It is probably there and most likely my mind is ignoring it.

For instance, you could face major legal issues if you accidentally (ignorance is poor defense, especially in the Peoples Republic of Illinois) charge a tenant more than what you were charged plus the state allowed fee.  

Misinformation or just ignorance.

At the time of purchase I was ignorant to the wealth buliding potential of real estate and purchased this property with no regards to ROI or investment value.

I don't know how well you know your market, but I am assuming you aren't ignorant and know where the good, bad and decent areas to live in are.

@Jon Holdman thank you for ignoring my short sale comment and clearing up all the questions I had!

I am brand new to REI so please forgive my ignorance with the question I’m about to ask...Why would you want to take that much depreciation (a little over 20% of the purchase price) if you only expect what I will assume is only a cap rate of ~10%?

Not only does this solve a lot of problems, the manager knows that 1) you care about the property and don’t want it to rot away and 2) they can’t ignore that house, because you are checking ... pretty much after the first time doing that the rentals look pretty good lol. 

If they say you have to provide them a copy of the lease, then that's what you signed up for.I recommend contacting the HOA, pleading ignorance, asking forgiveness, and begging them to reduce the charges to something more reasonable.

I have tried charging a $25 late fee but this doesn't seem to phase this particular tenant , she just ignores the late fee