To get technical, you will be going up against the Economic Substance Doctrine which states that a transaction has economic substance if: (1) the transaction changes in a meaningful way (apart from Federal income tax effects) the taxpayer’s economic position; and (2) the taxpayer has a substantial purpose (apart from Federal income tax effects) for entering into such transaction.By transferring your primary residence into a LLC, you would not be changing your economic position.

The resident is on a month to month lease.

Unless you are planning to buy a personal residence and that is your priority, I think it's a smart move. 

By outsourcing, they let private providers run all the risk should their enrollment demographic shift toward those who don't have to be in residence here.

I have three rentals attached to my residence.

I am reading a Robert Irwin book which suggests buying a home every 1-2 years as your primary residence, and renting out the previous residences as investments.

So if the average is 95% I’d underwrite to 93%-94% (physical...economic is another story entirely).As to your second question—resident profile changes are a painful process.

I am reading a Robert Irwin book which suggests buying a home every 1-2 years as your primary residence, and renting out the previous residences as investments.

and move into the former investment home and again never pay the tax while enjoying the tax free sale of your former residence.3.

I'm not sure that the residence we are currently staying in is optimal for an AirBnb.