It is perhaps because of this that I am fixated on the pickpocketing problem. I've received a lot of helpful comments and I will be putting much of what people have said into the thief and assassin characters, when I am again able to think with a clear head. This is the first time in days that I have felt up to writing anything.
There is a point that has been missed, however. Several have said that in their campaigns, their thieves most often use the pick pocket skill to get hold of things, like a guard's key or a specific item from an NPC. I must say I find this strange, since I never have players that do this. Not that I have any problem with the idea, I think it is sound. It is perhaps that I don't give keys to guards who can be approached in the open (logically, a guard standing outside a gate would be let through the gate by a guard on the inside, thus you would need the key to steal the key) or because I don't think to put valuable adventure-critical items in NPC pockets. If we as DMs don't create the situation where the pickpocket can solve the problem with pickpocketing, the players don't use that as the solution. After all, who needs a key? Doesn't a thief open locks?
My bigger problem, which I stated on the previous post, but which was passed over, is this:
- We can assume that pickpocketing is a way for a player character to make money.
- How much money ought a pickpocket of varying level succeed in obtaining from a total stranger, keeping in mind that we want to make the score matter to the player?
- How do we make the obtaining of that score difficult enough that the player can't just rob thousands of g.p. at will without risk?
Risk is, after all, the game. Without risk, I might just as well give the thief the money and have done with it. There HAS to be a risk that threatens actual death, or it won't cause the player to hesitate.
To encourage the player not to hesitate, the score has to be BIG enough that the player can't easily forget the presence of the potential take. It has to be mouth-watering. It has to bother the thief. This is the only thing that will encourage the thief to hazard the risk.
The sweet spot between these two points was the purpose for the pickpocketing table. The sweet spot is achieved by giving the thief additional skills as the thief increases in level. That only lowers the risk, which makes the take easier and spoils the game. The better alternative is to increase the size of the score, arguing that the benefit of the thief's level is NOT that the thief gets better at taking things, but that the thief gets better at finding things to take.
Presumably, a 9th level thief wouldn't walk from one side of a doorway to the other to lift 20 g.p. from a target. Why bother? Said thief already has pockets and hoards bulging with thousands of gold. I should have made the score size based on a die roll ~ like, say, a d10 per level. Then a 9th level thief might feel it worthwhile balancing a point of 6 against a take of 500 g.p. He might seriously risk rolling snake eyes again if the score was nearly 10,000 g.p.
It has to be understood that ALL game rules are seeking that sweet spot that produces the player's dilemma. We want the emotional rush that is produced by the sound of the ball rolling around the roulette wheel coupled with the near certainty that putting a hundred dollars on number 26 is sheer folly. The near certainty. There is a world of angst to be found in the word "near."
So we don't want rules that eventually guarantee a player's success. I understand this is what most DMs adhere to when creating rules for anything, the presupposition that as a player character increases in levels, their success edges towards certainty. No. No, no, no. We've got it all wrong there. The game is designed to ensure that increase in levels assures a greater variety of monstrous foes, a greater variety of obstacles and difficulties to overcome and a greater variety of ways to die. The game does not get easier for players who go up levels! In most ways, it gets harder. Much, much harder!
3.5e never learned this lesson, 4e never learned this lesson, 5e hasn't learned this lesson. It is why most games, played the way the rules say, suck ~ but in a very subtle way, in a way that has DMs and players scratching their heads and thinking, "This is all really awesome, except for this thing I can't quite put my finger on."
It takes a very self-aware DM to overcome the tendency to feed the player's hero-fantasies and ensure that the game consistently makes the player ache and flinch at the same time. Most DMs who can do this, I'm dead certain, don't know that they're doing this. It goes back to what I've consistently said: we don't know when we're playing the game well. It is such a hard game to know.