I'm California-based where there aren't any real deals in my area, so I'm exploring Detroit as an alternative real estate investment market - due to the combination of it being a strong market and my having connections in the area. 

I'd underwrite the deal as any other - make sure you are conformable with the quality & tenant base. 

While my sister and I will not have any issues based on our history and lives, the goal is to use this property as the learning ground for the final outcome: four duplexes---Structuring the property under an LLC or land trust could trigger a due-on-sale clause, so check with the lender before proceeding.

We are based in Milwaukee WI and have tenants from Milwaukee County and the City of Milwaukee and it's pretty much hurry up and wait. 

Are there any other areas I should consider based on my budget and purpose?

Do you have a specific revenue target in mind for hiring, or are you basing it more on workload?  

To remedy this for next time I am in the process of creating a design board that can be used as a base for future flips.

I was kind of skeptical, but seems this city/town is good place for STRs based on your response.  

Onslow County is home of Camp LeJeune (Marine base) so there is always a big need for more LTR rentals.

In the past 10 years, Ocala has greatly improved the employment base, adding tons of logistics and distribution jobs on top of the medical, service and equestrian jobs that we have always had.