Florida also have many more high end places than Oklahoma (we are much more of a blue collar city in my experience). 

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!

No issue with the city since lease is 30+ days.

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

What if the city finds out? 

@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.

Rare do I hear of recommendations but I do hear people asking.I would think in any big city you think about, a visit to a local NARPEM meeting or 2-3 visits would be a great idea. 

Like any city, there is dilapidated housing stock in rough areas that can cost more to upgrade than they are worth. 

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.

Our process server charges $40 within the city limits.