Animating them individually is fine for me, for now anyway.
So I’ve been playing around with it and tried putting the subsurf modifier ABOVE the cloth modifier to what kind of effect that would have. The movement looked a bit more fluid, but the baking took FOREVER. Literally 100x as long as when I had the subsurf applied after the cloth. Definitely not worth slightly better results in this case. I could see how it might be better for more complex scenes, though. Depends on what you’re trying to accomplish, I guess.
Is that fairly typical practice then? Keeping the mesh object for the cloth as simple as possible and applying “touch up” modifiers lower in the stack? I was surprised at how much additional time the baking took when I changed the order of the modifier stack.