I think that this somewhat exaggerates the difficulty. Both Maelstrom Storytelling and HeroQuest 2nd ed give better guidelines, for example, and neither of those games is published by a company with the same resources and design capacity as WotC.The problem is that Skill Challenges have to be very general where combat rules cover are specific.
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It's going to be incredibly difficult to make a set of deep, interesting, rules to that can cover these and more scenarios.
The task isn't trivial, but it is hardly that hard. The main problem with skill challenges is that they don't have enough axes for the player and DM to manipulate--both narratively and through the mechanics. Since most of the narration is supplied by the people at the table, a group that gets this can cover that side of the deficit. But mechanically, they will always be weak as long as everything is essentially a series of skill checks.
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For a quick example off the top of my head: Add "culture" and "resources" as narrative elements with mechanical backing. Then make the skill checks in the base system a bit more difficult than they are now.
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When you make a culture or resources checks (however those are done), what you are trying to do is avoid a skill check that is high risk and/or low reward and bypass/change it to another check more to your liking. Intimidate is your best skill and the skill challenge is infertile ground for such a check? Pick another high skill, or use culture or resources to move the ground where Intimidate makes sense.
Skill Challenges are supposed to be narratives, the die rolling aspect of the whole thing is simply a general accounting mechanism. There is no expectation that players will NOT change the context of the SC. In fact that turns out to be the most interesting part in any decent SC already.
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Advantages are one way that WotC has given us in the most recent SC rules to easily represent this kind of thing mechanically. A player takes actions which change the situation in his favor, he gets an advantage, maybe a check becomes easy, or making the hard DC gives an extra success, or a check can remove a failure. These are all possible ways to quickly and easily represent this. There are more sophisticated ways as well, like unlocking new skills.
And those are all bad design choices, or at least no answer whatsoever to problem I am addressing. It may or may not be a good idea to tweak/complicate how skills work, but doing so adds no appreciable mechanical depth to the system. And it would still resolve into defacto numbers that have predictable chances of success.
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Skill challenges, to give XP, should really have multiple types of levers with which to move things, and these levers should have different costs and risks. Then you quite easily get interesting decisions like, "If I bribe that guy now, we will get an easy in to the palace, but I won't have the money later, and we'll waste my pal's high bluff ability to lie our way through. On the other hand, if he blows the roll, we'll start out behind, and this is already a tough nut to crack. Hmm...."
Like I said, I'm sure a lot of DMs already do that. I certainly do. I'd rather have more mechanical heft backing me up, given what skill challenges are trying to accomplish, though.
I think that the 4e designers are trying to hint at the greater depth that you (Crazy Jerome) are looking for, but doing a fairly bad job of it.Ever seen the resource system in Burning Wheel? Or the circles mechanics, for that matter? Those are good examples of how a mechanic can invoke a different axis, be used more or less generically within its sphere of control, but still provide a lot more depth than the space it takes up would first have one to suspect.
We can't just lift those directly from BW for 4E. For one thing, the resources system in BW isn't meant to handle a constant influx of gold from adventuring (though it does have provision for such at times). What makes it work but still be applicable is that is conceptually tight on what and when it addresses: Do you have enough cash, favors, friends, loans, etc. to make this thing happen that people want that stuff for, or do you not? If you try and fail, what are the consequences? That kind of stuff comes up in the narrative all the time, and with 4E we don't even have the existence of profession skills or merchant skills in the way to use something like it!
I think that there is some scope to introduce mutliple dimensions of player decision-making while still focusing on skill checks as the principle mechanic for resolution, via either (i) secondary skill checks, or (ii) primary skill checks with secondary consequences.
AbdulAlhazred gives the example of unlocking new skills. This is a distinct dimension of decision-making, resembling some of what you talk about in your example of using culture/resources/circles to move the ground to circumstances more fertile for an Intimidate check. Certain uses of advantages might also be deployed in a similar vein - obtaining the advantage might require shifting the circumstances in certain ways, or an advantage might be expended to achieve such a result.
DMG2 also gives some ideas about how to bring extra player resources into the mix, which don't necessarily add new mechanical axes but do add new dimensions to the decision-making - for example, it provides an equivalence between gp spent and successful aid-another checks, and also tries to deal with encounter and daily powers, and rituals, as meaningful contributors to a skill challenge.
In my view, then, before new mechanical axes are introduced, what is needed is a thorough and systematic attempt to bring all this existing stuff together and give a coherent account from the designers as to how they see it all working, and how a GM and players can work through it in the course of resolving a skill challenge. For example, do the designers envisage skill challenges permitting anything like a "quick take" in Maelstrom - where a player can make a check that is distinct from the overall resolution of the scene in order to lock-in some more local outcome - or not? And what would be required to secure such a result (eg spending an action point)? I'd like some of these basic questions to be sorted out.