I'm an easygoing roommate and looking to cut costs and also have a more fun experience sharing space with a woman who invests. 

Find ways to cut expenses.

I've wanted to get into real estate for a long time but typically moving into that realm in a w2 position means a decent pay cut and probable loss of all the other good stuff.

But there is hope... if you drive through the 4th ward area, you can clearly tell which properties are owned (single family homes with kept lawns and neatly decorated) and which properties are rentals (usually a broken window or two, falling apart porches, messy yards)... the closer to the single family-dense parts in the 4th ward, the better chance you have of getting a rental property that hasn't been laid to waste that you can purchase for a fairly cheap price. 

I woke up today with plenty of "Price Cuts" from the listings.

One thing I have learned is people don't have a problem wasting your time!

BTW I have been successful petitioning the court however I wouldnt  waste my time doing it again. 

Stop hanging out with your deadbeat buddies who spend all day drinking, talking sports, and otherwise wasting away.

Open Houses - I always feel like I've wasted time by doing one.

I have been using innago and manually entering every expense for 11 units, huge waste of time, but I am a detail freak and like to know profitability by property.