So the plan we figure is cleanest is to have the LLC buy the property from the individual partner (writing check from LLC to individual partner, and recording a grant deed transferring title to the LLC).

Preferably, the adviser has previously reviewed this strategy so that it is not necessary for them to charge for time taken to research this topic.Monetized installment sales may be considered controversial by some.

It'd be great for individuals downsizing, new homeowners, or those just starting a family.

I like you prefer to buy an empty building.

From there it is a matter of how passive your father would prefer the next investment to be.  

We've had a few smart condo owners in Chicago realize their building is worth more as a deconverted apartment building than individual condos and vote to sell to an investor for far more than their individual units were worth.

I would prefer a safe first investment with a lower return to high risk.

What helps me is to think "Individuals" vs "Businesses" and not so much hard money lender vs. private lender. 

But I would prefer to just have the monthly net with a few doors as possible. 

After renting from a poor property manager, I'd prefer to never have to rent a house again.At the moment I have 2 rental properties and a primary residence.