Airbnb), Rent to own or simply sell it and use the money to buy a better performing rental property.

What I can tell you is that the musician with 25 1099s from 25 performance gigs is going to have a LOT easier of a time buying a house if there's one Schedule C for all of it, rather than 3 or 5 or 25 (in the real world that last example would typically be from someone doing their own taxes).

Perform due diligence. 

Let him review the mold remediation documents and perform a thorough mold inspection of the whole house.

That's all costs considered.I'm hesitant to let a moneymaker go to barely performing, especially since rental cashflow is my goal and to quit my job and make real estate my full time, but if it's in the name of expanding my portfolio I think it's justifiable.

I am a big sports fan and am excited about the Kansas City Chiefs recent Super Bowl win.

We wanted to perform due diligence to see if that type of capital expenditure was worth it.

@Jordan Santiago, I would pass on a deal that diluted my equity ownership at any point due to performance.

I need to keep looking for one that actually wants to perform the duties of their chosen profession.  

Not so detailed as to tell them how to perform the job, but detailed enough that they are bidding the work he wants/needs completed.