Originally Posted by Frumpkis
*snip* Trying to steal an object often fails the dice roll, so I just steal the gold and buy what I want. It's too easy. What they may need to do is put a limit on how many times you can pickpocket the same merchant, before they catch on and you always fail.

If a merchant (who make their living selling things!!!) continually gets robbed, it makes sense that they'd get more cautious.

Maybe the DC for stealing from them could go up 1 for every object stolen? (Possibly going back down by 1 every day they don't get stolen from?)
Or after getting stolen from a few times the merchant could mention in a voice bark or dialogue that "These parts are too dangerous and I'm losing too much money. If I lose another item I'll go have to close up shop"

Though I don't really mind being able to steal from merchants ad infinitum; if a player wants to play that way that's fine with me. As long as the game is balanced for not doing that.