You know what, the answer to questions 1 and 2 are the same, they only change when the wine changes. The stinkier the cheese, the more likely it is that I'll save it for a white wine. And with reds I love blues and cheddars, and I tend to prefer opposite ages: young cheese with old wine, old cheese with young wine.
On food? The only foods I put cheese on are tacos, some salads, and some Italian food. Those vary but are pretty usual--young cheddar on tacos, swiss cheese on spinach salad, parmesan or romano on Italian. That kind of thing.
My wine shopping and I have never had a problem. Just a perpetual race between the bankruptcy court and Hell.--Rogov