I think there is more work for pickpoket than just this ...
Personaly i would love to see a little bit more complex situation ...
Its easier to imagine in forced turn based situation ...
1) First of all, i would like to see stealing to be concidered bonus action ... that way "thieves", as advanced class for rogue ... could steal double amount of items per round, wich kinda seem acurate to me ... right now i dont see them to be anyhow more thievery, than arcane trickster, dex. focused rangers, fighters, etc...
Also it seem to me to be incredibly stupid, that our tief (no matter the actual class) can rob vendor off litteraly almost everything in 6 seconds window of opourtunity.
2) I would like to see merchant to do some perception check every turn ... there are people around him, so he have to be carefull ...
That way vendors can see that their goods is missing retrospectively, but our tief (if s/he is smart) can also steal completely unnoticed.
3) And finaly i would love to see that perception check to become easier and easier with either every round ... or every stolen item ... and with some valuable items to even easier it even more.
4) Failed perception check ... vendor have no idea he was robt.
Failed sleight of hand ... vendor automaticly sucess on perception check ofc.
Meaning:
You stole some gray item, perception check Dif. 19
You stole 5 arrows, perception check Dif. 15 (lowering by 1 per item, arrows are after all pretty small)
You stole some usual weapon, perception check Dif. 18 (lowering by 2 per bigger item, unless 2h)
You stole some usual armor, perception check Dif. 17 (lowering by 3 per even bigger item, or 2h weapon)
You stole some magic weapon, perception check Dif. 16 (2 per weapon, doubled for magic one)
You stole some magic armor, perception check Dif. 14 (3 per armor, doubled for magic one)
Not sure how implement gold stealing tho. :-/
Maybe dif. 20-1*(amount of gold/100, rounded up) ... meaning lowering perception by 1 with every 1-99g you stole. So, if you are extremely lucky, you can stole 1900g without noticing.
Either that, or just lowering perception check dif. by item value.
In realtime i expect situation to go the same, just faster.
