We had a tenant that moved in a roommate to help pay rent etc and 2 weeks after we approved his move in all of a sudden we are hit with the bed bugs issue.

Jon,I currently own a property off campus and rent to roommates.

I have a property that I have been renting to two guys as roommates for the last three years.

I took over someones lease that expires on March 31st and paid the entire remainder at $750 per month, so I got an awesome deal, and I've got a room mate, so my living expenses are very low. 

Whether it is a roommate or a stand alone unit, house hacking really is a great way to begin the real estate investment journey!

If you play your cards right you could potentially cover your entire mortgage with the rent from roommates, then you can put all the money that you would be paying in rent towards your next property.

If you're thinking sooner rather than later, multi-family maybe a better route as your future wife is not going to want to live with roommates - I know mine didn't. :) If you think that is not in your future, then you may not only be able to use your VA benefit to find a great deal on a single family home, but you could find a 5-6 bedroom single family home and make great rent by doing a rent-by-the-room setup. 

If she meshed well with the other roommates I would extend the term in the event she wanted to.  

I've put about 10k or so into it so far and i have a roommate moving in with me in november who will be renting the downstairs (bedroom, den, bathroom) for $750 a month. 

I am currently working a job making around 40K a year and am renting a place with some roommates.