The Midwest, including cities like Detroit, offers some of the best opportunities for affordable properties with strong rent-to-price ratios.

In the city of Portland (Oregon) they only allow us to run rental/criminal history if a tenant applicant isn't contributing to rent (if they aren't paying, we don't get to look at their finances). 

Since downtown development land goes for $30 million/acre, $100k imposed by the progressive city government for a 40 story building permit is a minor annoyance.

It's a lot of work upfront but once the team and systems are established it gets easier and as you get better you can expand to another city. 

Our logical process:1) Use Neighborhood rankings to narrow down area of city you want to invest in2) Focus on getting to know that Neighborhood(s), so you know the good & bad streets, block-by-block.3) Be patient to acquire properties on good streets that meet your buying criteria.Our rankings are done with a "bell curve" approach.

Every Week I scan the MLS, navigating cities and towns in South Florida that are friendly (and not friendly) toward short term rentals.

I'm not as familiar with Cincinnati, but I have seen many headlines about the city's growth. 

@Jesse Streng Great that you want to invest in the Detroit area but I encourage you to come to the city and spend a weekend here to get a feel for the market.

And it's not only homes, it's all the infrastructure a city needs.On the insurance issue, I think this may be the end of national carriers.

Doesn't cause trouble for you/neighbors/city/police.That's pretty much the sum of it.