Also, make sure to square away the utilities, find out if you owe taxes for 2021, as mentioned above get the data on the tenants.

If you can qualify comfortably and are willing to take the risk, then jump.Another option is to get into contract to purchase the new house, close and then sell the existing one which mitigates (reduces) the risk of owning two properties in a market that may decrease in value.

Since I plan on doing this for at least the next 6 months, I want to be as organized as I can so I can keep track of leads, contacts, and data.

That was 7 years ago so don't have any recent data on them 

Find the data at the following link:  Median Price Multifamily Aurora Elgin

Although it appreciated in value, I would not purchase another one due to lack of control to your property.

I see this in the data and also in my business: we work with a lot of relocation clients and the reasons (for moving to Milwaukee) are usually cost of living, followed by smoke (from the fires), water (droughts in the SW) or floods.

This means that during periods of inflation, property assets in your portfolio will simultaneously increase in value.

I haven't take the time to look at the real data on what's going on with the rental market in Chicago but our system has blown up with inquiries.  

This means that during periods of inflation, property assets in your portfolio will simultaneously increase in value.