What $10 wine goes with these $10 chocolates?

I'd probably drink Merlot with the milk chocolate, and then Ives Noir with the dark chocolate. Mild with mild, stronger with stronger, so neither the wine overshadows the chocolate nor vice versa.

But... really, that's just personal preference - pairing is subjective. As another poster said you might be overthinking chocolate.

Also, keep in mind that prices vary wildly depending on where you're from, so it's hard to ask to a global community for a "$10 wine". For example I pay the equivalent to two euros for a bottle of Ives Noir here, but I bet that in Europe it would be far more expensive.