Neonchameleon
Legend
No, for an inexperienced DM it could be tricky to handle that as soon as the players don't want to dress up, but use invisibility and silence and have the rogue use a rope to get the weaker characters over the wall. Or arrange a distraction to cover the noise the dwarf makes by doing a bit of arson on the other end of the town. Or decide they don't want to go inside but lure their target outside.
Yeah, I could react each time and adapt the skill challenge, but what for? It's still a useless and counter-productive framework for something that doesn't need a framework, since every decision, every skill used can open a completely different path that throws the entire skill challenge off its rails. Rigid win/lose criteria are not good for a fluid and open and complex situation.
Quite the reverse.
The skill challenge is not about the method it's about the result. It's a generalised framework for handling a situation with minor setbacks but a desired endgame. The start to the skill challenge is "all PCs outside the walls". The successful result of the skill challenge is "all PCs inside the walls and the guards not alerted". How the PCs wish to go about this is up to them.
As a rule I only start skill challenges when PCs have told me what their plans are. And the skill challenge is how I assess whether they complete the plan.
Not at all.
With a skill challenge the players just need to roll X number of successes using whatever skill they are good at (intimidate, bluff, etc.). It doesn't really matter what they do as long as they roll the skill they are good at.
If the PCs aren't engaging with the fiction they don't get to roll skills. Period. This is Rules As Written.
Now you can say that this encourages PCs to try to use the skills they are good at wherever they can find a good use within the fiction. I don't see this as a problem.
With individual checks it doesn't only matter that they succeed in checks, it also matters what they do. This is especially important when checks fail.
Agghhh!
A skill challenge is a narrative and mechanical framework that strings together a collection of skill checks into a coherent scene. Absolutely everything that applies to skill checks applies to the skill checks within the scene framed by a skill challenge.
You can't really have such evolving situation which skill challenges. The situation is practically static till the skill challenge is over.
Nonsense. The fiction is dynamic and unfolding in exactly the same way it would be if they were rolling skill checks that weren't in a skill challenge framework. And because their successes and failures change the narrative they open up the skills usable (or, more rarely, close them down).
To use an analogy, if skill checks are sentences that help you write an argument then Skill Challenges are the five paragraph essay structure. It might not always produce the best results, but it almost always produces consistent and clear arguments using your sentences. And if you want to put together a good and clear argument that looks professional under time pressure, using the five paragraph essay is a good place to start.