If the tenant complains (even if he feels everything was deducted correctly), he offers them 30% of the amount he deducted back.

The biggest thing holding me back from getting started is me feeling like i need more guidance.

You might have a challenge with tenants/customers feeling uncomfortable next to a prison so getting the local insights might be valuable to you as well. 

I'm not super familiar with the Charleston Market but I feel that the rental market is on the rise in West Virginia as a whole.

I may be paranoid but it really feels safer to me to see buyer / seller in front of me with the attorney in charge, for some bizarre reason, when a person who had an online $100 or less class to become a public notary has the seller / buyer sign legal documents, I don't feel it's a safe way of verifying their identity and generally speaking I feel conducting these large deals with a table closing when all parties are present is way better.. or at least choose an agreed third party to verify identity of all parties (like a different law firm) is that just me being paranoid or is it a legitimate scare?

Living with parents in Chicago suburbs but moving to Lakeview East (North side Chicago) next month to get a feel for living in the city.

I feel she might sue me too.

Feels like its smart to sell because if i pay for a new roof or hvac my cash flow will take a long time to get me even on that out of pocket.  

Invasion of privacy and likely "creepy" for the residents to feel they are being watched. 

Currently I am looking into finding my first property so if you have any leads feel free to give me a shout.