During my time in college I never lived on campus and rented four different houses with roommates.

You can rent out the spare rooms to roommates to build experience and save more money for your next investment.  

I usually do a roommate release form that they both sign.

That could mean renting extra rooms out to roommates or buying 2-4 units, living in one, and renting the others.

My wife didn't want roommates but was willing to have a second unit on the property, as long as it was private.3.

I need a roommate.

Quote from @Nicholas Schwab: Have you ever heard of a house hacker that provides substantial services to their long-term tenants (or roommates)?  

My intention is to live in the basement, rent out the remaining bedroom to a long term roommate, and run the upstairs as a full time STR.I'm aware that the City of Littleton has strict short term rental regulations, but they do allow STRs as long as I have a license and I am occupying the property.  

I have two roommates in one of the units, both of whom are in the military.

We have a lot of equity in it and don’t make much on it, so that’s why we want to sell.Can we choose not to allow another roommate, force them to move out if the lease is violated if they can’t pay, and move on?