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Assuming that the Sergeant of the squad was wounded and the player decides to do a look out sir. Assuming he passes it and the landspeeder of the squad is the closest model, how would this work?

Reread the RAS rules, and note that it states they split up and operate as different units. So it is impossible for this to happen

Correct me if I'm wrong, but I thought the speeder seperated from the squad. ( I might be mistaken as I only got to glimpse through)

The land speeder is not part of the unit, as per the Ravenwing Combat squad rule on p47 of the DA codex