What I did for the Shopping requirement was to rebook a non-chain hotel reservation I already had on Booking.com through the portal. Net cost of no money (since I was spending it anyways) and well over the $50 threshold.
Just got the wines yesterday and haven't tried them yet. Figured they were the same cost/bottle as the plonk my wife drinks anyways and they can't be worse than that.... Kind of a PITA, though, because you have to have a person actually sign for them. That will be the reason I cancel once the required timeframe from the first order passes.