Luckily, I was able to purchase a condo in a new development in Brooklyn in 2011, with my mom lending me a significant about of the down payment, which I still own and live in w/ a roommate. 

I have two new to the work force room mates who are looking to move into my apartment for rent.

Footnote: me and my buddies are all looking for a place together mid July, so this could be a really good time for me to make this move possible given the potential rent from 2 roommates. 

I was going to pay cash for my car but have realized I like having that cushion.)Student Loan $13k at 3%, $150/Mo ~90 months leftHouse Loan, 57k left at 4.25% %, monthly payment $500 including insurance and taxes, Roommate pays $400/mo so my effective payment is only $100.  

My current roommates are going to move with me. 

I did what you suggested and typed in a potential tenant's name into Google and saw an ad they placed for a roommate to take over their current lease.

In my 4-Plex, I have one unit with roommates who have been generating a lot of noise complaints from the unit below them.

Then, getting a roommate and make money?

It's not really what you described but if you can get in a duplex you could rent out one side and get a roommate to speed up the cashflow.

You can get an fha mortgage with low down payment because you'll be living there, then you rent the extra rooms out to some roommates and live rent free with a potential for cash flow.