I don't want to be a buzzkill, but have you investigated the legal aspects of this with a lawyer? One is the trend for people to claim squatters rights. A guy in Kentucky let some "friends" stay recently, they claimed tenancy rights, filed a restraining order and forced him from his house! It was in the news. He eventually got it back, but OMG.
Also what you are describing is an "employee" to the IRS. Required to be there and do certain jobs at regular times, live on site, using your equipment, etc.. If anyone gets hurt is there workers comp / medical, soc sec,?
And, what are your laws on employee compensation / housing? You can't hire people for room and board alone anymore or with minimal pay, without meeting certain wage requirements (I think federally, but check your state). Also by providing employee housing there's a whole new set of tenancy rules in most cases. You can't just kick them out. Some states are very weak, others you'll have to evict, and housing value as compensation is capped at absurdly low amounts.
I had a guy work for me for ONE day flipping a house. 22 months later (24 mo statute of limitations) he sued me for a "back injury" and failure to pay (one days work). Luckily, we were a licensed company, with insurance, and outside payroll. He never returned for his pay, a check was mailed to his LKA and returned. Payroll still had the check, in the sealed, cancelled envelope in our file and the money still in our payroll account. I had three sets of lawyers on it. My own lawyer, my insurance, and a workers comp guy I hired. The WC lawyer took one look at the guy's lawyers name and laughed. He said, "This guy runs a WC mill, and does this all the time." They wait until just before the SofL expires, then file cases long after people forgot about them. We ultimately proved fraud but the DA would not bring charges and the insurance in the end paid them around $30,000 to go away. These people know this is the game and how to play it, we don't.
Anyway I'd talk to a lawyer(s) first and have some iron clad agreements in place.