Make sure you verify the labor and material costs you are paying, I mean absolutely sure because you really do want to understand his skin in the game. 

Cleveland has world-class: orchestra, theater, museums, heath-care ( Cleveland Clinic and University Hospitals ), top-ranked universities/colleges (Case Western Reserve, Cleveland Institute of Art), multiple Fortune 500 companies.

The tenant was a nightmare who ended up breaking their lease, threatening to sue me multiple times and just tying my stomach in knots.

It's a numbers game that requires many offers and also requires a little luck. 

The way I see it, unless they start tracing your IP address to your computer's location and triangulating that way, OR AirBNB starts forcing you to provide a unique identifier like a SS# to open a new account and then somehow verifying it (You can still have friends and family have accounts this way) and using a blend of strategies to make sure you aren't gaming the system, it will be very hard for them to enforce this for those who are motivated to get around it...

Once you get above five units the game changes and it is outside of the wheelhouse for most real estate agents.If you're looking for larger 30+ units then you should connect and network with commercial multifamily brokers in your area.

Wholesaling is mostly like any other market with a low barrier to entry: it's filled with people who have no skin in the game. is it possible?

@Nick Zias I know several people that own multiple homes in MSP.You need to do it because you care and have the money be a secondary goal.

Before I do this I want to learn as much as I can about the real estate game so that is why I'm here.

I'd also get multiple bids and numerous interviews to see who is knowledgeable in that particular situation.