You need someone to battle both the HOA and the mortgage and YCG, sounds like a lose-lose for you as you mention there's no big paydays, I assume this house is in StoneBridge, the HOA there is a nightmare. 

No loan, no payday.

If he is unsuccessful, then he is basically getting use of the land for the taxes (no really all that bad of a deal probably), but he might not be getting that big pay day by getting marketable title at the end of the AP term. 

We drug our feet to buy us time to get the permits sorted, and when we finally showed our plan to the court, they approved it because it was a win, win, win: The heirs got something when they weren't going to get anything, the bank got way more than they would have got in a foreclosure because we improved the property, and we made a nice pay day.

After one buyer backed out and we sold it to another buyer they ended up with a big pay day achieving an ARV 34k over what we expected solely due to new comps and appreciation in the area.

Even more active, is development & construction of all types of commercial properties, single family fix n flip, etc. with a LOT of moving parts, but bigger paydays on the back end.   

Since Contractors tend to live paycheck to paycheck I only want to give him enough money to get the job completed and he can have his $40,000 payday once he retails the property. 

Not to mention the new hire worries less that they are gonna get stiffed on payday because for all the know their check comes out of the payroll company's account. 

Put them on the payday rent payment plan.

I have way too much anxiety that if I am not adding people to my list of buyers and sellers every available moment, I am not getting closer to my next payday.