.: Hello all,I’m looking for some advice on a real estate decision.

What information I should be analyzing to help me make a decision on where I should start.  

First, I'd determine whether you like to be active (managing your own portfolio of rentals as you are today) or passive (letting go of control and day to day decisions/operations).

You get as much objective information about them so that you can make an informed decision. 2.

Here's a link to the data: https://mred.stats.10kresearch.com/infoserv/s-v1/vwxv-Zs5What this data shows at a Macro level is that the Chicago market is doing fine, but the market is too large to use that data to make any decisions about where you want to house hack.

Talk to your insurance agent and be sure you're covered.

I put property taxes 6k/year on each(Even though that's way higher then what it actually is, but the county tax estimate says its around that much for each) and for insurance, I just put 1,100/year on each.If there's more info needed let me know.

I purchased flood insurance on a Zone A property in July this past year on a house that had previously flooded. 

Was it the best financial decision ?

All in all - owning a place to rent to other people is a business, and business decisions need to be made based on that cold hard facts and not on an emotional basis, unless someone wants to quickly go out of business.