I currently live in San Diego, Ca. but have been looking in the midwest, mainly Iowa, Indiana and Ohio, for properties. 

It is currently my primary residence and was a great house hack but I’m now considering moving out to live with my girlfriend nearby in her condo.

Our first purchases were ones that we lived in and added value while we learned.  

I live in Detroit but envision running the investment as a business, not a third job: Pay top dollar for the best PMC.

Thing is, you need to understand it's going to a difficult way to earn a living.

After living in the property for a full year, we have come to terms and accepted that this is not our ideal location.

If you live there and are currently renting, then there still is a pathway to house hack say a duplex and better your situation.  

I own a single family home in Socal that my wife and i currently living in.

Nicholas, if you're look at the Ohio market you should definitely be giving Detroit a look as well.I live in CA and invest in Detroit.

Although I still think conventional is the better option, I wouldn't put 20% down if I didn't have to, unless you know you'll live in/own the house long enough to recoup that additional $.