If you want the box + tarot card yourself then you already know the answer: yes it matters.
Of course a box and tarot card don't actually have any effect on the actual shoe, but any time we buy something, most of us want everything that it is supposed to come with. If your boy is looking for max resale money, of course he would want to keep the original packaging. I know that if I'm paying $350+ for a pair of shoes I want anything and everything it came with.
As far as being disappointed in dude, it can go both ways. He could look at you like "Hommie knows I'm in a tight spot with my car so I need this money. And he's gonna trip off a box and card?"