If your friend is seeing the requirement to buy it on the 2nd item on the Premium Track, they just need to progress the Season questline a bit in order to claim it.
If your friend is using the account that actually now owns the Deluxe and they didn't make any changes to Cross-Save after the application of the purchase, they should have the Season Passes applied.
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Thanks for your help! We were able to play the first mission as a team and do the group activity -- and he was able to get the cache of loot in the HELM so that was all very surprising to see it was still asking...maybe because he was playing while I was fire captain? I will tell him to try playing on his own... thank you for your fast reply, I really appreciate it! -mike