I canít say there is a lot of science that goes into the order I make my pies, but itís not random either (they donít always get posted in the order they were made).
The order evolves on the fly. A mushroom/white truffle is almost always first as it is my youngest sonís favorite (heís the one who makes the sauce and is most into pizza). A Margherita or some variant of is usually second. Brussels Sprouts is typically third (these are my two favorites). Pepperoni or sausage is usually fourth (back to the boyís favorites). The fifth pie is usually something with a salad on top. The 6th pie is usually something new or a pie I really want to get right (by this time, Iím pretty dialed in. The last few pies are often the best). The last few pies will be another Margherita, some sort of pie with meat or seafood, or something new.
As for the wine, my wife does not drink a lot, so itís generally what Iím in the mood for. Some days thatís something that pairs really well with pizza. For my taste, this is an mature wine with earthy, leathery flavors and not a ton of fruit. Iíve been in a good place with older cabs lately. On days like this, I drink most of my wine at the table when Iím eating. On other days, Iím in the mood for something like a giant hedonistic Australian shiraz Ė a wine you can stand a fork up in. On days like this, I drink most of my wine at my prep table as Iím making the pies and Iím probably drinking water or a [fill-in-the-blank] and coke with my pizza. It would be unusual for me to pair particular pizzas and wines. I also generally stick with similar wines throughout a particular evening, though I almost never open two of the same bottles in a particular evening Ė what fun is that? The one exception to the similar wine thing would be that from time-to-time, Iíll open something light and sweet with spicy pies like bacon or pepperoni and jalapeno.
Iíll have to think about your last question some.