I also feel I could manage it myself.

Feel free to connect. 

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. 

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

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

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?

Maybe selling into something with better numbers or lower headaches is the right decision for you, however I want to encourage you to speak with a few different experts along the way so that you can account for all of the important variables. 

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.