Do you have a strong lease that you understand and can enforce?

This is only one area of real estate that should be addressed, and it typically involves premises liability/property management type claims.

There is a Fund of Funds involved.  

But, understand DSCR loans are only for investment properties, not for a primary home you might want to buy in the future. 

Being deeply involved in the local real estate market, I stay connected with wholesalers, realtors, and local investors who often share opportunities.

I would also encourage you to get involved in networking groups in the Chicagoland area as well as listen to the straight up Chicago investor podcast.

Doubt this is the final version as the "smart" people in the city understand Detroit is coming back and needs to keep welcoming investment instead of putting up roadbloacks:)As many STR landlords have learned in other cities and in oversatuarated areas, it's always good to have a backup plan!

Get a development standards book so you can understand what and why a engineer should do something.

Understand Proposition 13 for property tax benefits, local transfer taxes, and strict tenant and rent control laws.

It boils down to education and understanding more than anything.