The wireless activation password "not set" is for Enterprise Activation only so dont worry about that, it has nothing to do with calendar sync.
As for this users issue, if they dont have access to DM then you may want to try re activating them on the BES. The best way to do this is to remove and re add the user from the BES [clearing the BB info and stats if prompted] perform a security wipe on the HH followed by Enterprise Activation.
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