Err, not that I am against rogue characters (in fact I am quite in favour of them), but have you noticed the fundamental flaw in roleplaying pickpocketing?
No, I don't see that flaw that you see. But let's have a look at alternatives first before I come to that:
1. We ban people who try to roleplay rogues and keep this game to the grinding/mining/money making/leveling business that it is now.
2. A technical solution is implemented which
a) leaves the victim no chance
b) is prone to abuse as everyone just can do it.
No, my approach was to follow a fundamental principle of all roleplaying games and that is to play together and to ensure that everybody has fun in doing so. I think my approach leaves the most freedom to everyone. You don't want to be stolen from? Fine, just state that your purse/pouch is neatly tucked away. You are open to the roleplay of rogues? Fine, then why not give the rogue player the chance to continue his play and decide during this play if he is to succed. If you think that the thief player has done a nice job the why not reward him with some trias? If you think that the situation was such that it was impossible to steal then you caught the thief red handed. The only flaw here is that it requires a certain sensitivity for the situation. If a thief gets there are three choices:
1. He finds an excuse and is believed. End of theft and no reward for the thief.
2. He runs away, which could lead to a chase. If not caught on the chase the thief has to lie low for a couple of days. No reward for the thief and he is considered a fugative with a chance to be recognised.
3. He gets arrested. Depending on the sentence this could mean the end of the character or just a couple of days offline.
All three outcomes can lead to interesting follow up roleplaying.
Roleplaying is about the interaction between persons. Pickpocketing is by definition something that should be done without being noticed (unless of course you insist on being well known for being the worst pickpocket of all times and people automatically tucking away their purses as soon as you enter the tavern). So, how do you expect people should react to "/me looks for things to steal"? If you do that announcement ICly, it means everyone will also ICly know about your intentions (which obviously is not going to help you steal anything). If you do it OOCly ... well, then it is not roleplay by definition.
In other words: There is no logical reaction to your actions, as the whole process does not allow for any (IC) interaction.
Well, let's start by examining what the engine offers or better what it does not offer:
1. The engine allows to set a description. Theoretically you could describe in there how your character looks and what he is wearing. How many players use this feature? I would say about 30% but you can correct me if I'm wrong. The drawback of this feature is that you would have to change it once you change your "outfit". So the description can hardly be used to see what others wearing.
2. The engine show what kind of armour you are wearing and what kind of weapons you are holding. Does it show any other item such as purses or pouches? No.
Ergo I have to ask what the victim is wearing. I could do this by using tell but then again if I'm checking up a victim there might be a chance that somebody else notices it that's why I use the "emote". I leave it to you which one is the better solution.
What the character is wearing (and which is visible) is a totally IC-thing. Me watching is a totally IC-thing. It is only the lack of support from the engine that makes this process a little bit awkward.
So up to this point I don't see any problems with mixing IC and OOC. But let's explore the rest of the "procedure".
Let's asume I have met someone that signals that he is open to play out a theft by stating that a purse can be seen hanging on the right side of his belt. So I am getting close to him, making sure that I have his back to me and that he is distracted, e.g. trading with someone. This is still my character doing it so it is IC. I may have a close look at the purse now (Same as above so still IC). He describes that it is an ordinary which is fastened to his belt by the strings. So I decide it would be the easiest to just cut from the belt(still IC). I am slowly drawing my dagger making sure that it does not make any noise. This is still IC. Let's have a short break here to exmine the possible reaction of the victim up to this point. The victim could be that type that gets nervouv as soon someone enters his aura(IC of the victim). In this case the victim would have turned around and the theft would be over at this point. Or the victim has a very good hearing and heard that a drew my dagger from the sheath. It would then have turned around as well to see who was making the noise and I would be in trouble to explain why I did draw a weapon. Both being totally IC.
But let's press "play" again, asuming that the victim did not notice me so far. I carefully try to grab the strings to avoid tucking at them while cutting. I then carefully cut the strings. This is all done IC. Let's stop again and see what the other side could do. Maybe the victim is sensitve to touch. It then could notice me either grabbing the strings or while I cut them or when the weight of the purse is gone all of a sudden. Being caught here would mean serious trouble for the thief. But whatever, everything is still IC.
If the thief has not been caught up to this point the transaction of the booty takes place. Once again the engine offers only little support so we have to use the trade window. The thief usually walks away inconspicuously at this point, or gives the booty to someone else and remains where he is looking as inconspicuous as he can, but everything is still IC.