Well, super rolling has two basic benefits: one, it lets you pull off a Hard difficulty check, and two (though this really depends on the group), it tends to have some roleplaying impact. It might be improvised as a mechanical benefit — if you pass a Diplomacy check by 20, you may wind up making the target particularly impressed, and the next Diplomacy check gets a +2 bonus. Or maybe it's just a straight-up roleplaying thing wherein if you pass your Acrobatics check by 20, you look damn good. That is of zero utility to some groups, but in other groups, looking damn good is not only fun, but critical successes and critical failures can help shape how you see your character.
We used to have critical successes on skill rolls in the 3.5 game - if you first rolled a 20 and then confirmed with a second successfull skill roll, you got something extra out of it. That way one of my characters got taken for a goddess on a 20-20 diplomacy check, got involved in the religious life of the indigenes, and started her own cult - not to mention got a few religius conundrums herself... wonderful roleplaying times.
It got removed in the shift to 4E as "not in the spirit of 4E" and "incompatible with the skill challenge mechanics"... Now its just "what's the tally on this skill challenge..." - individual rolls does not matter


I dunno if that's the intention. It seems more like the desire to make your skill choices relevant outside of appropriate roleplaying situations, and relevant in any combat you get into. It doesn't seem to be so much "man, I wish I had more reward for beating a check by 10" as "man, I wish I could use my training in Bluff in some way against this behir."
The problem with that is that you probably already has something better in your regular powers for the behir...
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