A combination of extremely tough long term tenant protections and the economics of short term renting being a lot more attractive. 

Check out this recent thread on LLC’s, it’s pretty eye-opening that of all the very experienced investors on here, with centuries of investing experience combined, the consensus was that LLC’s are not needed for most investors:  https://www.biggerpockets.com/forums/926/ Of course gurus will tell you that you need one before you even have a single property, because it makes them sound smart.

I am currently invested close the Marywood University where I do have a combination of family and student tenants. 

The labor forces used are rarely licensed and insured, are the bottom of the bottom and paired with the cheapest materials... a losing combination. 

As the portfolio grows, we’ll be able to implement gradual, strategic adjustments to rental rates, particularly for tenants in need, without undermining the overall financial health of the endowment.Phased Returns for Investors:Investors will be repaid through a combination of rental income and profits from other high-yield activities, such as property flips, during the early phases of the project.

For example, I mention that every adult must pay a $30 application fee, pass my credit/criminal background, make a combined income of 3x the rent, and whether or not the property accepts pets.

Combine that with rates that are near high for this century.  3 things could solve this 1) RE prices fall (that would be bad for me) 2) rents increase a lot without RE prices increasing similarly (this would be bad for tenants) 3) rates fall a lot.  

Tulsa offers a fantastic combination of affordable housing, a growing job market, and a strong sense of community.

My gut says you probably want/need separate policies for the different entities at the very least - the purpose of having them is to keep things separate in case of a lawsuit, so combining insurance would pierce the veil and allow someone to come after everything. 

The combination of OOS + S8 is toxic.