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[MENTION=42582]pemerton[/MENTION]
Thank you for all the number crunching! You beat me to it! I'd XP you if I could.
You confirmed what we, or at least I, suspected - that skill challenges can't be directly ported into 5e because the math is different and there is more magic swinginess built into the system, not to mention PCs helping each other (and all the other ways they might gain advantage).
I think the assumptions in a 5e skill challenge would have to be:
Thank you for all the number crunching! You beat me to it! I'd XP you if I could.

You confirmed what we, or at least I, suspected - that skill challenges can't be directly ported into 5e because the math is different and there is more magic swinginess built into the system, not to mention PCs helping each other (and all the other ways they might gain advantage).
I think the assumptions in a 5e skill challenge would have to be:
- The odds are built around PCs with skill boosting magic, Expertise, and/or ways to gain advantage.
- Easy DCs should be the backbone of the challenge. Easy DCs aren't necessarily "easy", but are easy relative to the overall difficulty of adventuring tasks that aren't assumed to be automatically successfully. IOW if its worth rolling then there's a significant risk of failure.
- You probably don't want super long (e.g 10 or 12 successes required) challenges in 5e. My guesstimate is that requiring about 7 successes is the maximum practical limit. Of course, changing the failure limit is always an option, but if you're willing to change the failure limit, that breaks the math.