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Another clarification as I work my way through the rulebook.

A Slaanesh Herald (on a Seeker Mount) joins a unit of Fiends (Beasts). The Herald positions itself closest to the enemy as the unit receives fire.

Can the Herald use Look Out Sir! to move wounds around the Fiend unit (2w each) on a 2+ (same save as Fiends so whether it is before or after saves are taken at this point is irrelevant).

I do not see anything prohibiting this (and it is what has been suggested for Blood Crushers w/ Khorne Heralds)

Edit: Pardon the addendum but I am unclear on Fleet as well - it states "A unit composed entirely of models with fleet can re-roll one or more of the dice when determining the run moves and charge ranges."

I am taking this to mean: on a charge of snake eyes you can re-roll both dice, but on a charge of 6, 1 you can re-roll just the one.

calypso2ts wrote:Can the Herald use Look Out Sir! to move wounds around the Fiend unit (2w each) on a 2+

I take it what you're actually asking here is, can you allocate those wounds to different models so that each Fiend can only take 1 wound at most? I believe you can, I don't have the rulebook on me but from memory the wording states that you get to choose which model in the unit the successfully rolled LOS is re-allocated to.

calypso2ts wrote:"A unit composed entirely of models with fleet can re-roll one or more of the dice when determining the run moves and charge ranges."
I am taking this to mean: on a charge of snake eyes you can re-roll both dice, but on a charge of 6, 1 you can re-roll just the one.

Correct - the wording "can re-roll one or more of the dice" overrides the general rule that you must reroll all of them.

Yes. LOS allws you to allocate to any model within 6", and does not require you to wound a model that is already wounded.

You can reroll one or more dice. If you reroll 1 you have complied. If you reroll both you have complied.