» Sun Sep 09, 2012 11:46 pm
It has always seemed to me Shady Sam is a grey area type of NPC. He doesn't want to go all the way and affiliate himself with the Thief's Guild, yet he desires to make a decent living. Selling lockpicks and poisons (etc.) is not against the law, so here merely provides these services full-time, and is therefore in competition with regular shopkeepers, who only carry such items in smaller batches.
It's like the corner store that sells drug paraphernalia, small weapons, and girly magazines. These are all frowned upon by certain members of society, but they are not illegal. What you do with them is your business. And if "Your Business" happens to be illegal, the corner store (i.e. Shady Sam) wants nothing to do with this.
It is also interesting that we cannot persuade Shady Sam, and to get onto his bartering menu, we have to move the D-pad sideways instead of down. Well, this is how it is on consoles, maybe PC it's different.