I currently own a townhouse in Brick that I purchased 4 years ago and I am planning on renting it to my current roommate in the fall but using the calculator it's only cash flowing around  $40 a month.

Maybe it'll be a house for yourself where you have roommates.

If it were me, I'd probably buy a primary in ATX with 5% down conventional loan, live in it for a year with roommates, then rent it out when I move to Florida.

I collect rent from a roommate in the first unit and also collect rent from the second unit.

With Apartments.com I can automate rent payments, have the security deposit paid, and have tenants upload their proof of renter's insurance.Challenges of living with other roommates and renting by the roomWhen living with roommates there are always challenges.

I assume you are talking about multi units not actually roommates.

Do you know if a roommate is something she would even consider? 

Only buy something you can afford on your own however, then rent out the spare bedrooms (if you wouldn't mind living with roommates).

Unlikely, but your probably don't want a roommate named Bubba for the next 30 years. 

Since my family runs our rentals through an LLC and this property needed a lot of repairs, my roommates and I have paid a market price rent to my LLC since I bought it and we have treated the property as 100% rental on both sides, claiming all income, expense, interest, tax, and depreciation deductions.