There's also at Costco a cheese package that has an old cheddar that is creamier, less aged and suggested pairing is white wine, and an aged crumbly cheddar that can be paired with a hearty red (Cab Sauv I would think).
What you have there is a good starter for you new adventure.
Have you ever considered pairing chocolate with a nice Ice Wine.
The delicate sweet nature of the wine pairs well with the slightly bitter undertones you get with a good quality is a site to check out too... had a Meritage with 85% chocolate.
Sometimes your pairings can be too similar and make you feel like your eating your meal and drinking the liquid version of it.