I would make sure financially you have a good base and then connect with a local agent

If you need financial help, ask under the "Finance, Tax, and Legal" forum.

House hacking is financially a no-brainer and no city in the US (including Chicago) has more duplexes than Milwaukee.

And what today - probably near 8%.

Still, if you aren't whittling down the number you are analyzing financially to a small subset you see before deciding what to do, you are missing an essential part of getting to the tipping point of expertise in your field.

I have learned that in today's world of information you do not need to limit your investment to just markets you live in or normally travel to. 

It’s quite appealing as a long term investment - even at today’s rates.

I am aware of companies like Pad Split, but would prefer to have a more traditional company overseeing the day to day since I am out of state the majority of the year.

Improve your credit and financials so lenders are willing to take a chance on you.

I encourage you to define your financial goals, as real estate presents numerous possibilities.Building a strong foundation of knowledge and connections can significantly impact your success in real estate investing.