Some buyers don't want your tenants who may or may not have been screen properly but some buyers like the attraction of having income on day one. 

Additionally the suburbs have higher taxes compared to Chicago proper.  

Also, be sure to consult a CPA about the timing of transitioning properties to an LLC to avoid potential complications with financing or taxes.Take time to compare multiple lenders and products that fit your strategy.

As long as you're making payments on time and have proper insurance on the property, banks are happy and don't want to call a loan due. 

Quote from @Brandon Croucier: We have a direct product that does portfolio/blanket loans, even if the properties are out of state .How many properties are in the bundle?

I have zero stress having the systems in place with the proper people in place to manage my day to day operations.

Also you can see their overall productivity.

Two business days after that I get an email saying they received my info and will pass it along to the "product team" to process the request.Later that day I get another email asking me to verify my identity again. 

Take ownership of your mistake and learn to do the proper due diligence recommended above😊 

Thanks for input - He's insisting that because it's a DSCR loan, and because the size of the deal is too small to go into their "Portfolio Loan" product, that it has to be two separate loans.