Anyone who says failing can create the most interesting stories is an extremely wise tabletop player. If someone is saying you need to pass every check or succeed every check or not fail every check, odds are they're new to the genre or ignorant and close minded. Anyone who's played tabletop RPG's for a long time can tell you with complete and absolute certainty that their most hilarious adventures, stories, and experiences came from everything going horribly wrong. There's nothing particularly special about making success a near certainty and having everything go according to plan no matter how intricate you make the plan. But having there be a real chance of failure and hitting it and all of a sudden everything's going wrong and you have to salvage what's happening? Now THAT'S where DND and tabletop get truly interesting.
