The person I would seek advice from is a CPA about this. 

Managing five rentals can eat up a ton of time in any given week, often at times that are inconvenient to you and your personal interests (family, hobbies, travel, etc.).Of course you can manage on your own.

Id have a lawyer on hand, this person seems like they will escalate issues once you notify them you aren't renewing their lease.  

They paid their portion of the rent.I have found a lot of investors bring their personal or political feelings into the investing conversation. 

Are you interested in S8 because of a personal reason or you think it's the next "hot" investment idea?

It also gives you multiple work surfaces so you can have more than one person in the kitchen without getting in each others' way.

You’re still going to be personally sued when something goes wrong. 

Probably not a good person to hire, maybe let your bosses know. 

So the question becomes based on their individual and personal tax situation what is the estimated tax burden they'd save? 

One of them I have used personally.