@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.

I did not realize one of my units had the 7-night minimum but that currently is a requirement in my city, I do not always follow it.

Here is some info: SF STR FAQAssuming the info is up-to-date, it must be your permanent residence (you must live at the property for a minimum 275 days a year), you can rent unhosted a max of 90 nights a year, you need a business license, and you need to pay the city $925 for a STR certificate.

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.

I believe Alexandria city allows it but portions of Fairfax county do not allow it. i would go option 1 personally. 

Quote from @Brandon Foster: Hello Ryan,STR is do able in the north county area but there are a lot of rules and regulations.The city of Oceanside right now will not allow anything STR unless it’s west of pacific coast hwy.This is changing a lot too so you need to be aware of that in your plans.Carlsbad is super strict too but there are some condos that are still available to do STR in.Medium term rentals are as safer bet but way less profitable.

Chicago cap rates are actually much higher then other comparable sized cities.

Verifying last 2 years of rental history and income extremely important to find the “best of the worst”.Make sure you understand the Class of properties you are looking at and the corresponding results to expect.The City of Detroit has 183 Neighborhoods we’ve analyzed.DM us if you’d like to discuss this logical approach in greater detail!

Our process server charges $40 within the city limits.

Quote from @Reyna Ayala: Hi first time landlord to a duplex in new city.