from what i've heard of within Canada, there used to be a six month requirement before you were able to use passes. however, that has been lifted, and you can now travel from day one now. I don't know if it's any different in the US.

i'm afraid i don't know what the actual costs of the trips are like.

and just quick scan of the ac website shows that they have positions posted for ORD and BOS (in their cargo dept)

and skywalkerLAX is correct. if you can get a better paying job elsewhere, go for it because the airlines will give you stand-by passes, but not the means to use them like you would want to.