If you can't fail a skill check, there should be no roll. Same as most DMs won't make you do a skill check for "I sit down on a chair".
Rolling dice implies that there's a chance of failure.
Failed skill checks on 1 break d&d by making skilled people fail regularly just as less skilled people do.
Nope. 1/20 is much less regular than 5/20 or even 19/20. More skill doesn't mean it always works, only that your chances are higher. And if you are skilled enough that it always works, then there should be no roll.