I think it really depends on the person that is asking, and that is something you will only know.
He could be the nice guy that offers to pay for your lift ticket out of kindness, but wants to invite another friend and was hoping you'd be nice enough to pick him up since you live closer.
Or he could be the guy that is always asking you to do things for him, and he puts his mind at ease by occasionally rewarding you for your efforts through payment, directly, or otherwise; in this case, a lift ticket.
I'd just step back and try to take an objective look at the person making the request and make the decision of what to do from here on that. I wouldn't recommend doing anything before, or during, the ski trip, as they seem like fun plans and there's plenty of time down the road to address these things. As long as you actually do address them at some point if you intend to.
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