Based on the above points, you asked us (experienced investors) what would WE decide.  

We have made money buying properety based on cash flow (lower priced) rented out for a period, then selling to an owner occupant. 

I see you are located in Royal Oak, that is the area we've actually been looking at as I'll be based in Warren at the Arsenal. 

It's a loan based on your revenues.

Only place I felt "safe" in CA was on base.

I'm sure it was highway robbery - it certainly was based on the man-hours it took - but when you are in a desperate situation, you do what you have to do to get yourself out of it.  

Those numbers are arbitrary unlike taxes and insurance and they vary based on age, condition, area, landscape, PM, and other things.

I would recommend you begin researching Chicago based meetups as there are a bunch of really good ones.

Property taxes will likely be reassessed based on the transfer value, so confirm local rules to anticipate potential increases.If you hold the property for at least one year, you can use the equity as collateral for a construction loan, aligning with your long-term financing plans.

Airbnb is very algorithm based and despite the popular opinion its not hard to stay in good standings on the algorithm.