Robbing every merchant blind is basically my ultimate goal, because they also recharge. So you can continually rob them blind.
I dislike how Larian tends to make stealing the ULTIMATE skill - to impossibly rob everyone blind to get the best loot. More fantastical than magic itself, more rewarding than fighting an ancient dragon without a fraction of the risk or effort. For me this is an exploitable anti-roleplaying loot pinata system when I feel like it should be roleplayed more as a moral question.
You said it more eloquently than I did but what you said sums it up nicely for me. What's the point of the rest of the game if everything you want can be obtained through thievery? And again, I realize one could choose not to steal everything but knowing you can still cheapens the experience of the game.
That said, I want to be fair here and say that stealing is not the only problem with the game's economy. I am sitting on almost 6k of gold I have accrued by more conventional methods and I've pretty much bought everything I could want out of the vendors' inventories. There's just not enough things worth buying that I have found so far so you end up piling up gold one way or another.
