Crosby, worth touching base with an attorney because tenant law can be so local, but that being said:You have the right to screen and approve the people that live in your property (adults anyway).

Or, does it make more sense as you hit that size to hire someone that answers only to you to manage it and provide bonus incentives for them to keep everything occupied with good tenants?

I LOVE seeing my prospects face to face and sizing them up, I'd hate to have no idea who's living in my property.

Guy was trying to “Size Me Up” and I didn’t handle it well, as I never handle being “sized up” well.

Does anyone have advice on the best times to begin advertising, examples of leases in similar situations, and best practices for screening tenant-roomates? 

The return on equity is low and damage too costly if you don't screen well.If a nicer place I would explore selling it and taking the (probably mostly) tax-free gain and invest or otherwise use the proceeds for their benefit.As Ashish points out, heirs would inherit the house at it's current value at death whether it's a rental or not. 

Each Village depending on size has someone that regulates rentals and associations.

While you probably can't re-screen the tenants (check the leases,  some have a clause allowing for that)  you might be able to infer if any occupants are employed,  going to school or otherwise showing signs of responsibility.Agreeing with prior posts I would be VERY CAUTIOUS about terminating the leases for any reason even remotely relating to their sec8 status,  especially if they are otherwise in good standing.   

Or there is a version for 2 to 4 unit small buildings as well but then down payment grows to 25%.Or if you agree to live in it for 12 months you can do it as an FHA 203k rehab loan with as little as 3.50% down on 1 to 4 unit properties and use future rents to qualify for the loan size needed.

The area is 15+ acres up to 100 acres, my choice on the size.