Even expensive bags don't all hold their equity indefinitely, and true for Dior bags. He should know this from the Rolex secondary market except for certain models.
I saw your first post hehe and to answer your first post - that’s just how our household runs.
And this man has never made a bad purchase. He sold one of his Porsches last week and made $30k over what he paid last year and his favorite Rolex he paid $26k for and it’s selling for $48k on the resale market right now. He sees literally everything as a money game and always wants to come out on top. He’s an oil salesman by trade and I think that the fact that he loves negotiating and does it all day colors his view of the world.