RPGMemes

For most skills, there low level human equivalents in the real world who will never "choke under pressure" once when doing the thing thousands of times throughout their life. When we're talking about one of the heroes of a tale that are also "the best of the best", I think it's ok from a literature, fantasy, or gameplay standpoint for them to have a 100% success rate despite the fact that a failure risk would be possible in the real world. This is doubly true (DM point of view) when failure would be uninteresting or mess with suspension of disbelief. If an ace pilot is trying to fly through a bad storm to land where the firefight is going to happen, he bloody well makes it. I'm ok with "success with complications" on a 1, but the complications should be fun as well. You land ok, but the wind that hit at the last minute caused some damage to a wing. You might need to find another way out" or even "unfortunately, you weren't able to fly evasively enough because of the buffetting winds, so they know you're here.

Nobody wants Skyrim syndrome, where a master thief gets caught pickpocketing someone (we Bethesda players do something called save-scumming to keep the immersion). I used to go to a pickpocket show at the local renfair and the performer never got caught. And he was not a "master thief".