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So, if a landspeeder can see target and is within 18 inches, at whirlwind gets a +1 to hit it. So:

1. If a character is the closest target to the landspeeder, can the whirlwind target it? or
2. Can the whirlwind target it as long as the landspeeder can see it?

Trying to get my head around the interaction between datalink, target units out of LOS and look out sir rules. It came up at a tournament recently, answer to point 1 from the TO was "yes".

This stratagem in no way changes if the Whirlwind can target a Character. The normal rules are still in effect.

 alextroy wrote:
This stratagem in no way changes if the Whirlwind can target a Character. The normal rules are still in effect.

So are you saying that unless the character is the closest unit to the whirlwind, it can't target it, even if the landspeeder can see it and/or is closest to it?

No. I'm saying the Look Our, Sir rules applies as normal. From the FAQ:

Page 219 – Look Out, Sir
Change this rule to read:
‘Models cannot target a unit that contains any Character models with a Wounds characteristic of 9 or less with a ranged weapon while that Character unit is within 3" of any of the following:
• A friendly unit that contains 1 or more Vehicle or Monster models with a wounds characteristic of 10 or more.
• A friendly non-Character unit that contains 1 or more Vehicle or Monster models.
• A friendly non-Character unit that contains 3 or more models.
In all cases, if that Character unit is both visible to the firing model and it is the closest enemy unit to the firing model, it can be targeted normally. When determining if that Character unit is the closest enemy unit to the firing model, ignore other enemy units that contain any Character models with a Wounds characteristics of 9 or less.’

Cool, good to know.