Folks move in who don't need space anyway and benefit from an on-premises on-call nursing stationI've researched shipping containers only slightly but feel that or assisted living could be a draw for this type of housing community.

What I would do is pay the Operating LLC a Management Fee from each LLC to do the  Property Management for the other LLC's, create a salary or a draw from that LLC so you create an actual profitable entity.

The trick is deciding where to draw your lines.

There are properties with "polluted title."   

My only concern is he doesn’t have an agent and all the documents he draws up himself.

Contract agreement, you should consult an attorney and have one drafted for your specific requirements (at least including a written scope of work, any drawings/specifications you have, construction schedule, warranty, payment schedule, license and insurance requirements), and have it amended over time as issues arise. 

@Tom S. 100% agree with you that interest only is much simpler and easy to draw up however, with this not being value add deal I don't suspect there will be enough equity to refi and pay off the debt (50k).

Then,  I'd hire an experienced 10-25 person Civil Engineering firm firm to estimate timeline and cost for the zoning, planning, utilities, etc. and to draw a layout of the lots, streets, utilities, etc. 

So my renant, who I eveicted after 18 months, left a hole in the wall, walls filthy with child drawings (painted right before move in and unable to rent without extensive cleaning or painting), yellow dirty tub (which was recaulked right around 12 month mark), filthy stove, and grease on the backsplash area behind the stove.

The biggest draw is I have no clue where to start.