Thank You for the input, it's confirmed there is not a straight forward traditional mortgage option.I'm looking for a property in the 100k range.

This is straight from the CFPB website: "Additionally, for 60 days from the date your loan servicing transfers, your new servicer cannot charge you a late fee or treat the payment as late if you sent it to your previous servicer on time or within the applicable grace period."

Many tenants will cut their nose off to spite their face and move, rather than accepting a fair increase:(What does Zillow say the rent should be?

I like the idea of getting a great deal, so should I take a pay cut, invest in getting my real estate's license, go the CCIM route, and find a broker to sponsor me until I'm a CRE broker and earn of the commission and get into bigger deals as a GP?

Cut your losses the first time they miss a payment and start the eviction process.

I’d recommend listening to the straight up Chicago investor podcast for local information, going to the variety of meetups that are in this great city, and meeting a lot of the people posting here. 

Is it a straight 1.5% on the monthly rent after 5 days ($23.25)? 

Cut expenses and work, no way around it.

I don’t understand why I would jump straight to getting the note done with as my first option.

Hey James,Ah, I see where you're coming from—given the Chicago winter, cutting off electric isn’t really an option without risking serious damage like frozen pipes.