FrogReaver
As long as i get to be the frog
How so?
I seem to recall that in the original example the DM (or the player?) even rolled to see how badass the target hapened to be, and in the example got pretty much the badassiest possible result; followed by the best when the target took it all in good humour and just repaid the wedgie with a little interest.
I think you've missed a lot from that part of the discussion. I don't blame you, a lot was said and quite similar but different things said by quite a few as well.
@Elfcrusher was talking about auto ruled failure with no roll by the DM or by the player to determine the NPC badassness. That's the context for the above comment. Essentially it's what you said in the last part of your paragraph.
A bad DM would just arbitrarily decide the target was a mega-level Monk. A good DM rolls some dice to see what the target's made of, and runs with the result.