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)?

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.

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

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. 

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

Even though no prepayment is possible, we are quoting a lot of 1, 2, or 3 year prepayments. 

I'm guessing because most newbies have never gone through a situation where they invest in unsecured notes (if we can even call these notes) and they stop receiving payments.

,Buying, renovating, and selling is a great strategy, but here are a few things to consider:Start with the Numbers: Make sure you know your ARV (After Repair Value) and work backward to calculate your budget, including purchase, renovation, holding, and selling costs.Financing Blindspots: Even if you’re buying in cash, plan for potential delays or overruns in renovation costs.