My biggest concern (if I was you...which of course I am not) would be his gambling.
You want to know if he's gambling beyond his means (can he afford to blow $6000 dollars or did he just blow all his money and now can afford to pay rent, bills, food, etc?). Does he have a severe addiction? His he going to be hitting you up for money because he's gambled all his away (I'm pretty sure you don't want to be supporting him and his problem...if it is a problem).
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