Which is ok because you have a regular job and a couple of properties. 

It has a strong and diversified job market and relatively high quality of life for the midwest.

In MF investing is it more important to be a:Spreadsheet ninja Or Good operator?

Don't pay seller late this is important to be able to refinanceGo find a w-2 job today, any job that brings in cash or gig money not uber that wrecks your car.

We are at a point where we are scaling our operations first time and have external investors who are willing to put in $$.

Recently started a new job in Plain City.

I am not planning on quitting my day job anytime soon but rather my hope is to gradually grow the amount of income I am able to bring in over the next 5 years to be in a position to make Real Estate my full time gig. 

My girlfriend and I are looking to move to Chicago some time in 2025 (likely the fall) for her job, and we are looking to buy a small multifamily property (2-4 units).

The biggest cons I found were in operational risk.

Hey Jason, the best way to find these distressed properties (off-market deals), you have to either do it yourself, which is a full-time job calling and building relationships with these cold sellers, or find investor-friendly agents/wholesalers sourcing these deals for you.