Well, if you want to know the size of a hole, the easy way to do it is with a pin gauge. They come in a set, little cylinders of known size, You see which one goes in the hole, and that is your size. For the screws, as @rogart63 says, measure with a caliper. Vintage pin gauge sets made for watchmaking show up on the bay every once in a while.
When I'm sorting an unidentified set of something, I just start dividing into big/little, or short/long, or something like that, and keep dividing until each size is in its own little group. If I then want to know an actual size I will compare against a known example. If I want to know thread pitch, for example, I might hold a screw up to a tap to see if the threads are similar.
Not hard, just tedious. I have to be in the right mood to tackle some of my junk piles :-)