Then, I'd work with a reputable accounting software like Quickbooks or Wave.

From your first picture there is a plastic pane that slides into place so that it can stay closed/locked and keep the dog (or other animals) from climbing in and out.

Having airtight financials on the property, a well written business plan, potentially even estimates for immediate repairs from reputable contractors will all help, once you find banks that can work with your situation.

He's looking to connect with a reputable RE agent who can work with him on his criteria and view potential deals as he deliberates what property to purchase.Looking forward to recommendations!

If anyone knows any good bankers I would love to talk to them because my normally reputable bank seems to be like a deer in headlights here.

Go with the advice @Nathan G. gave and find a reputable PM to handle all this for you. 

@Dan Heuschele An infinite return via getting all your money out constantly is completely different from a TRUE 250%-400% Tax free return as I have created with this method after my 2500+ hours of studying and being mentored by the biggest most reputable faces in real estate, i.e the equivalent to what would take someone that's as motivated as possible 5-15 years to learn if they had a full time job (I spent 18-19 over a year of 8 hours a day 7 days a week on learning how to truly be a millionaire and successful in all aspects).Thanks for the tips but you did not answer my question, and I know all of the things you said obviously and I will adjust to the best possible thing available in my situation after deliberate knowledge on each individual matter and having a physical mentor,community and tons of other sources of wisdom and knowledge going into all of this before I start. 

Looking for a reputable Property Management company in the Chicagoland area.

Careful with this strategy, though, because you don't want to get a reputation for locking Seller's into contracts and then failing to close if you cannot find a Buyer for your contract. 

Besides finding a reputable property manager, what are some other things to consider when dealing with purchasing properties thousands of miles away from us (the investors).