The big pros are the strong job market (lots of major employers), good population growth, and still-reasonable entry prices.

My recommendation would be to choose potential markets - in several price points - that have strong rental demand and year-over-year rent increases and that also are in markets that are appreciating. 

If you're working with an investment brokerage, I'd recommend tapping into Tampa and Central Florida markets too—areas like Riverview, Wesley Chapel, and Brandon have been strong for both flips and long-term holds with steady demand.

I have strongly considered managing on my own in the past. 

Here are a few additional strategies that might help mitigate risk if you decide to rent the property:Hire a Strong Property Management Company: While you’ve already spoken with some PMs, consider finding one with extensive experience managing single-family rentals in Cook County specifically.

If you feel like you have a strong argument, you might as well try it's the way I look at it.

Not a strong argument ;-) I still had to pay off the loan to cure the DOS. 

We hear from a lot of out of state investors that Milwaukee is a great place to invest in real estate due to its affordability and strong economic growth. 

I’m reaching out with an investment opportunity in a real estate flip project, and I’m currently seeking a limited partner to join me.With a strong track record of successful real estate investments, I am looking to partner with someone who shares an interest in capitalizing on the potential of this market.

We’re working in a smaller market like Cornelia, GA, where comparable sales data can be limited, and want to make sure we present a strong case to lenders.