I'm glad I followed my hunch on the pirate guy. Turns out he's highly collectible by Disney enthusiasts. This is a souvenir that was sold at Disneyland back in the seventies, before all Disney memorabilia was so uniformly branded. It was made by a company called "Randotti", and says "Randotti 1973" on the back. So the $50 sale prices I was seeing on eBay were not a fluke.

I'm less sure about the silverplate, but like I mentioned in the post, I have another antique piece (was my grandmother's) I've been trying to sell on eBay for several months with no bites. So I thought combining the pieces in a lot might increase the likelihood of a sale. If not, it only cost me $4.

Great tip for the pencil sharpener! I was wondering how to go about spiffing it up.