Additionally to that I am looking to expand into 3 other markets but I have boots on the ground in those areas.

Since it's trust ownership, there are some additional benefits. 

Many newcomers spend their first few years working under a sponsoring broker, and during that period, the broker often earns a significant portion of the revenue.

In addition, there will be a ton of high school seniors coming to campus Jan-March to tour campus etc to decide if they would like to attend etc. 

He's a legit guy and we are now on agreement to purchase an additional 66 acres. 

It certainly has a large dependency; you are at the mercy of that one OTA.In addition, unless you are at ideal occupancy, alternate platforms can fill some holes.  

I'd spend maybe ~$60k of that money.

Verify if there are additional adults or other violations.

Is there the option to rent a bedroom on your side of the duplex for additional income?

I have found some information that might be helpful John.There are government backed programs like Fannie Mae Homestyle Renovation Loan and Freddie Mac Home Possible Renovation Loan, in addition to the FHA 203k loan.