Question said:Theres also the "issue" of how the level 20 wizard can get stumped on a simple knowledge roll, while his apprentice knows everything about it.
The other problem with treating opposed grapple checks like attack rolls w/regard to auto-success/failure is...what happens when both combatants roll natural 1's or 20's?myradale said:Even if the RAW would suggest that a one is an auto-fail and a 20 is an auto-success for opposed roles, I would strongly suggest house ruling it otherwise.
Otherwise you can end up with the exceedingly ridiculous situation of a pixie trying to trip a storm giant and having a 10% chance of success (1/20 chance of a natural 20 for the pixie, 1/20 chance of a natural 1 for the giant)

(Dungeons & Dragons)
Rulebook featuring "high magic" options, including a host of new spells.