Thank you very much for your responses.

Swag, I have a double ski bag (looks pretty huge) so it still will count as one non-oversized item together with a bag containing 2 pairs of boots?? (boots are heavy). And another thing, what are the chances they will be undamaged? will the airline take care not to put them on the bottom of the luggage pile?

Do you need to just present the card to get the free luggage? (we can get another card in DH's name as an authorized user just for our trips). Would that work?