Then again, I know some people that are absolutely terrible with money that have succeeded in real estate carrying a large amount of debt.It sounds like you are referring to you and your significant other when you say "we."

I'm pretty confident, not terribly scared or excited.

Its a 6k sq foot house in a terrible state of disarray.

That looks terrible

For the most part she hasn't been a terrible tenant but it's just time to move on and now she's giving me hell for it.

I tried hiring a management company a couple months ago and they did a terrible job.

I noticed my credit cards (I have only two) have terrible rewards programs. 

@Karan Rekhi this is all i do. i only rent by the room. anyone that tells you it’s not worth doing is wrong. be careful about town ordinances. the town i am in only allows 4 unrelated people per unit.as far as finding people, i do all of that although your incentive idea isn’t terrible. i have all multifamily and i basically position tenants together that will fit well. also, sometimes females will be uncomfortable living with males. for the most part, if you can get like minded people together you will be fine.yes, depending on your class of people, you will get some drama. do your homework on your tenants and vet them well and always talk to the previous landlord. happy to help you here. just let me know why other questions you have. you will have growing pains with this strategy but once you get the hang of it, it will be very valuable.

That said, you would probably be better served first finding work that didn't feel like a prison sentence rather than pinning your hopes on RE, which is a long-view investing strategy rather than a short-term gambit to escape a terrible job. 

Thanks @Matt Maurice, I already made the mistake first hand of renting to family and that went so terribly you would have thought thatI had learned my lesson.