The longer you wait, the better, even though there is no direct language in §1031 about doing a cash out refinance after the purchase.

My local Airbnb rep said the algo does consider cleaning fee too so try to be lower or even with your competition. 

STR can be exciting from many angles - Cash Flow, Appreciation, and best of all.. having a place to visit while renters pay down your mortgage (even near the beach!).

If you pay more, you won't meet your metrics and will probably have negative cashflow and/or equity.You may have to make 10, 20 or even 100 offers to get one accepted at the price that meets your numbers.This is what all investors did BEFORE the Great Real Estate Crash of 2008-2010.

Does anyone have experience with this (even better if in Chicago)?

What would you think for the side gig, LLC or not even a corp as i can do sole owner?

BiggerPockets also has a calculator to analyze deals, and I highly recommend you start this as soon as possible, even if you are not ready to buy.

Even with long-term tenants, you’ll still have turnover costs when they leave.

For me, even a 7% rate on my primary home would not want me to pay it off.

Even with multiple units, with current interest rates and a competitive market (prices have continued to rise even with higher interest rates) think the Madison market is a stronger long term ownership strategy, where the bulk of your return will come when you sell from appreciation in rents and property value.