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It's hard to say; the auctions that I've seen do best have been something that was LE and/or rare and/or hot trend (PODM, Brave, Up, Tangled.) Lots of people like Jessica. Lots of people like Stitch but there's a bit of a saturation in Stitch auctions at the moment. 🙂 Remember that the key is that it's not enough for it to be a really nice pin; it has to be a really nice pin that a lot of people want. Who have decent pins to spare to bid on. (Myself, I'm running out of traders to spare, so I'm bidding on fewer auctions.)
I think you might get the most bids on your evil queen sorcerer hat. Maybe the Jessica postcard/pin if it's on the postcard, maybe the one with the photo of Sleeping Beauty's castle.
I'm not the expert though. That title belongs to Goofy_Moe. 🙂 Check out the sticky thread with his auction tips if you haven't already; there's useful stuff there.