But it feels a lot like gambling to me, and I'm a terrible gambler. :)I hope you'll take this in the spirit intended, but it sounds like you are trying to keep all your options open.

Mainly because I am not good at it, and feel it is just gambling.

I think maintaining open lines of communication with the tenant and family will help the situation tremendously.You're taking a gamble, but it's one I would probably take too.

She won't be able to keep up with his spending, or gambling problem or whatever it is.  

If you were single, no kids, I would still say not enough, but the gamble might be a little easier to swing. 

If you’re rents dropped 20% you should still be in the positive long term or you’re gambling.

That's why I'd just take the $34 gamble. 

However, I honestly think it's more of a gamble than real estate is.

This guy is a gamble you should not take.I'm really floored that anyone here would even consider renting to this guy.  

Then, he'd tell me that so and so had been gambling, and so and so is into porn, and so and so got a rabbit, but we can't kick her out because then we'd have to tell her we found out by going through her garbage.