@Chris, certainly for the one I'm living in I'd be lucky to have two roommates that would even put me close to breaking even each month, but if I was to just buy a separate one, I'm really fortunate to have a lot of strong connections with people that need short term leases in the area, and I know what kind of premium they are use to paying for those.

I wish I had know more about house hacking back then, I would have rented out the other rooms either to long term roommates or AirBnB.If you are serious about starting now there are a ton of things you can do.

My closing date is set for April 30th and I am in the process of searching for roommates.

If we have an established tenant who is adding a roommate we only do criminal.

You would be surprised how many people enjoy the roommate model.

IIf you don't have time/don't want to clean rooms though, you might want to strongly consider just getting roommates. 

You can setup individual roommate accounts where they pay their portion separately.

During academic year it may be possible since some tenants look for their own roommates so they rent altogether.

While I was working here in Alaska I rented a two bedroom condo and rented the other room on AirBNB instead of finding a roommate and it basically paid for my rent.

Do I get landlord insurance AND renter's insurance with the roommates?