If you don't think you could re-rent it in 4 months - assuming you're not renting out some specialty penthouse on the Upper East Side - then you've got a bad place. 

In my current residence, the upper unit was 100% rent ready aside for some general cleaning.

Since you are working for a property management company you do have a leg up there but its not a guarantee. 

Very hard to find turn around properties in the upper midwest at a reasonable price.

Very hard to find turn around properties in the upper midwest at a reasonable price.

I would get turn key really nice place vs this fixer upper. 

Explore residential construction loans and buy yourself a "fixer upper".

With your drywall experience it could come in handy with flips or fixer uppers (first that come to mind) but the possibilities are endless.

My calculator isn't bullsh*ting me ( although certain "Gurus" on YouTube might be).I can certainly see buying a property with neg cashflow due to extremely poor management, then turning it around to make it profitable (those are usually the best deals in the end if they pan out), but you wouldn't (or at least shouldn't) be buying those "fixer uppers" at a 3.5% cap.In my example, I chose a 3.5% loan interest rate. 

I am looking at fixer upper multifamilys that I can get an FHA loan to house hack.