Central Florida, especially Clermont, Orlando, Lakeland, and Tampa suburbs like Riverview and Wesley Chapel, offers solid rental demand with strong growth.

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

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. 

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.

High LTV purchased at retail (off mls) has large initial negative cash flow- regulations are tenant friendly.  

Typically, the initial upfront for the rehab is either cash or a high interest loan (hard money or private). 

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

Is it better to keep adding equity by doing work on the houses while I'm renting them then refinance to recover the initial down-payment to reinvest into another property or to pay down the heloc?

Simplicity: TDAs require minimal effort after initial setup, making them attractive for those seeking stress-free investment.For investors like myself, seeking both stability and growth, combining a TDA with real estate investments creates a diversified portfolio.

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.