Advantage means there's only 1:400 chance of double 1's. But yes, it does happen. It happened on some silly DC4 item after I had cleared everything else of worth.
I then opt for violence, draw OA the _opposite_ direction I want to flee, hide and flee. Latest time I was still exposed, so Lae'zel shot a Darkness arrow. I've stolen plenty of these.
Eventually the reputation lost from times caught will close the trader, but I'm fine to move on then. If I wanted to fix reputation, I'd have to get my thief to donate money, and then steal it all back. However, I'm not stealing from reputable traders, so don't care.
If I really wanted to get efficient, I could recruit a halfling thief hireling. Their lucky trait rerolls 1's... Not a bad idea actually.
