Aldrick Tanith
First Post
It's not hard at all to create a character that can hit on a 2 every time. With a few re-roll abilities, it's possible for such characters to go several encounters without missing with an attack. Honestly, I think it is more likely for someone to build this type of character than they are to build one with a max skill in anything.
However, I have encountered a player that put everything possible into diplomacy such that hard DCs were unfailable. We always just treated as if her diplomacy was magical compulsion. (The character's Words of Friendship power, which gave her an additional +5 diplomacy once per encounter, even had the charm keyword). When the bard convinced a guard to let us through so easily, we just assumed it was because every word that came out of her mouth was dripping with arcane power (also why Vicious Mockery could literally kill people or knock them unconscious). It was a really cool and flavorful way of explaining why she could easily beat a DC 40. Your mileage may vary with martial characters, of course.
I agree with that assessment. At a certain point, if you raise your skills high enough, you effectively have supernatural powers. Whenever I think of insanely high skills, I always think of epic skill checks and "Swimming Up A Waterfall". Mentally, the very thought of doing this is impossible, silly, and ludicrous in the extreme. The only plausible way to have it make any sense at all is that it's supernatural.
This makes me think of the essay "D&D: Calibrating Your Expectations" by Justin Alexander. I think it pretty much covers how super high skills should be viewed from the (real world) perspective - they are beyond the ability of anything we could ever hope to achieve.