Outlaw Class

[Obnoxioussnipes]

Hey guys had a rule disagreement with the family.

For his Outlaws ability Dirty Rotten So-And-So "When Bad Stuff happens to a non-outlaw, go up a level. If he dies, the level you go up can be the winning level."

Two questions on this.

1) if the non-outlaw loses the run away but the bad stuff is lose your headgear and the non-outlaw doesn't have any headgear so nothing happens does the outlaw still gain a level?

2)if the non-outlaw loses the run away to the monster "Sheep Ones" where the Bad Stuff reads "None. They may be the servants of the Dark Gods from Beyond Time, but they're still sheep."
Does the Outlaw still get his level or no because the bad stuff is none?