So, if your character had knowledge (lower planes), diplomacy, perform (singing), and perform (fiddle), you could use the first three skills to attempt to modify your final perform (fiddle) skill check.
First 3.X let's you do this with synergies and aiding another, so that's nothing new.
As for more rolls being more dramatic, perhaps...but in a pure statistics sense, you're more likely to fail a sequence of rolls at 75% chance of success for each roll than a single roll at the same odds- cumulatively, the skill challenge drops the odds of success to around 42%. Unless you do your math properly, a skill challenge actually increases the likelihood the PCs will lose.
In game mechanics, and thus, in games, give me the single roll every time. I'm much more confident that a GM can look at a test of skill and say "I want the PC to have a 75% chance of success at this task" and do the math for a single roll than doing likewise for a sequence of 3 rolls. Heck, depending on the dice you use to determine success, you may not be able to do that completely accurately within a system: the odds of succeeding a sequence of 3 rolls at 90% chance per roll is 73%...and 3 rolls at 95% chance is 86%.
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