It takes a few days for the money to hit my account, but that is a small thing compared to the convenience.

Have you compared the appreciating cash flow on the duplex to the potential savings on your current mortgage over 1,3, and 5 years? 

Sounds like a challenging but rewarding project!

Document the time you spent on the property compared to others, especially if you’re trying to qualify under the “100 hours and more than anyone else” test.

Leverage magnifies return. 3) The effort involved in adding an ADU is comparable or larger than a rehab associated with a BRRRR.

My risk profile is moderate - medium risk reward.

Once you commit to this, it can actually be quite rewarding to provide housing to tenants.For contract renewals and rent increases, the first step is to familiarize yourself with local laws.

You can compare both options and see which makes more sense with the rate you'd qualify for.

Additionally the suburbs have higher taxes compared to Chicago proper.  

It's important not to get too caught up in the details; use the analyzer to compare one property to another.