And when I wanted some extra monthly income, I brought in roommates and learned about leases. 

And he's got two roommates so they should be able to help him out.

The tenant reached out with their intent to get a new roommate.

We recently purchased a home to rent to my college sophomore and her roommates.  

Then you can have a conventional roommate situation and save money towards the next down payment.

@Johnny Wolff Would say it depends on the city.We used to manage a property in Royal Oak, Michigan under the same "roommate" concept as you.

@Ryan RuncheyThe bookkeeping for this specific property will likely be difficult.This appears to be a househack as you purchased a personal residence but also have roommates to help with the rent.As a result, a portion of the expenses as they relate to the house are personal in nature and non-deductible.Items such as real estate taxes, mortgage interest, etc are all pro-rated.On-top of that you are doing the BRRRR which indicates that there is rehab involved.Portions of a rehab are currently deductible, capitalized or non-deductibleCurrently deductible - payment for an area of the home that is a tenant area.

zillow, realtor.com, facebook marketplace, put notice out to your friends and family you are looking for a roommate.   

So, yes keeping utilities in your name makes sense as these are not roommates with 1 lease.

He and roommates could live on one side and the other side he could rent out.