Thanks for all the information, everyone. I decided that as much as I want to try to get to the bottom of this myself, I don't have the energy right now, so I dropped my bike off at the shop with new wheel bearings, sprockets, chain, brake to install and then they're going to mess around with it and look for anything else that needs fixin'. I feel a little silly because it's only a couple hours work probably, but I just have too many projects and necessary home problems to solve now (water damage to my house's exterior is a bigger problem than a noisy bike). I did visually confirm that yeah every one of those parts is worn and needs replacement; we'll see if that's the end of the list, or not.
I got all the parts from Classicmotorworks, and they shipped fast!