If you pick the right roommates it’s also relatively passive and you get built-in friends.

In this environment, when courts do open up, they may be very considerate of a tenant who left because they were being forced to allow new roommates with no way to know if they are a health risk, so I wouldn't count on more than the security deposit.  

The benefit comes with tenants that are difficult in other ways, like sneaking in unapproved roommates, noise complaints from neighbors, consistently paying late, failing to maintain the lawn, etc.

Unlike young roommates I rent to that sometimes party into the night, with friends coming over taking parking spaces in the neighborhood, they're quiet stay at home types. 

I'd get them out, then advise him that you no longer want roommates and that you will not fix or maintain anything or renovate until a proper agreement is in place. 

Maybe I should have mentioned that initially I will live in the property (because of owner occupancy requirements with the VA loan) and have a tenant as a roommate......

We do have to use their application form.If someone moves in later (roommate, boyfriend, etc) we only run a criminal check, which we run through the state patrol.  

I would (1) write a letter to the current tenant stating that rent will go up $50 per month as there is an unauthorized roommate residing in the home. 

Like I’ve seen in my market and it’s likely the same on others, there are just multiple generations and/or multiple families living in one home and as a whole able to qualify and pay the high mortgages (parents with kids moved back home, grandparents living with kids, roommates, a room or garage converted to rentable studios, etc).

It was dumb luck that I flipped it and made 75k but it did help to have two roommates paying me rent.