If you're paying the entire purchase price and all closing costs with essentially a "no questions asked" line of credit, you're essentially a "cash buyer" from the POV of most sellers and agents.If you try to get a traditional mortgage 5 seconds later to pay off that line of credit, my underwriter isn't going to consider you a "cash buyer," because you aren't, but that's a different topic.

And States are pissed they are not collecting revenue - cpexecutive.com/post/report-short-term-rentals-costing-states-millions/?

It means you set the rules in your lease and you follow them from the very beginning, consistently.If the tenant pays late on their third month and you decide to waive the late fee, you are essentially telling the tenant your rules are negotiable.

I am not expert, and I am sure there are plenty that would have something to say about this... but essentially I decided to take a long term stance for my first investment, that's more on the safe side. 

A) Home specs * It is 4100 sq ft total and is essentially 2 homes in one, due to the basement apartment.

You're essentially paying your Tenant $600 to sign early when there's a very good chance they'll just sign it at $850.Nothing has been signed, so write up a short, very clear explanation/example.

https://www.amazon.com/Paper-Profits-Beginners-essentials-mortgage-ebook/dp/B06Y4C7X6Y/ https://www.pprnoteco.com/wp-content/uploads/2016/08/Intro_to_Note_Investing.pdf Finally, check out NoteMogul which has a very reasonably priced intro course to note investing. 

Now that you have made some essential repairs, will the property continue to need things fixed or are you good for a while?

No way would I want to deal with those tenant laws and high property taxes.The state of Illinois is essentially bankrupt.

Having recently obtained my real estate license and Property Management Master certification from the California Association of Realtors, I’m seeking that essential “real-world” experience in landlording/property management.