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Does Stadows of Fear apply against the first attack on EACH opponent suffering a fear affect or just the first attack, period? The way it reads implies it's against each opponent who's feared, if you hit multiple feared opponents such as through cleave, AoOs drawn by movement when frightened, etc...
Thoughts?
It's a lot easier to answer your question if you quoted the relevant abilities or linked them.
Your enemies’ fear causes them to jump at shadows, diverting their attention.
Prerequisites: Hidden strike +2d8 or sneak attack +2d6.
Benefit: The first time each round that you hit a creature suffering from a fear effect, you can deal hidden strike or sneak attack damage as if you were flanking that creature (improved uncanny dodge and other effects that prevent flanking also prevent a hidden strike or sneak attack from this feat).
It's a bit ambiguous but I think it's intended that it can be used on multiple enemies in a round. I say this because there's an easier way to write "once per round". For example "Once per round when you hit a creature suffering from a fear effect".
That may just be me reading far too much into it, though. As written it's "the first time" you hit a creature, not "the first time" per creature.
"The first time each round that you hit a creature suffering from a fear effect"
lets break it out:
the first time each 'X' that you 'Y' a 'Z' suffering from 'V' then ...
it's seem to me that the words "the first time" are connected to the words "each X" (each round) not to "Y" (hit)
if it was your way then it would say:
"the first time you hit a creature suffering from X each round..."