Thats a fair question, James!

There are rental management software programs you can leverage at a fairly reasonable price, which is what I used to get started (I'm still a newbie).

This will be an architecturally interesting building on 2+ acres with power gate at the road and fairly long driveway that sets the house out of sight from the road. 

Just like any other relationship, communication is key. 

Relationships and communication is huge and that's what we try to focus on.

He has another brother that is part of the Trust and he is okay with what my dad decides; he isn't involved at all but my dad wants to be fair in the situation and it would be fair market value for the property and do everything above board.My wife is a realtor, so we have the benefit of her selling it.

I would be focusing on cleaning up bookkeeping, communication portal with client, vendor list management, payment processing, etc. 

Even local title companies are turning down business for land sale without a very clear and open communication of all parties.  

True and fair enough.

Regarding the one month of rent Placement Fee, this is fairly normal.