I've downloaded lots of different liveries for various cars, tank cars, coal, all sorts, but when I load into a service usually none are chosen, just the stock ones. Also it seems like nothing is working for substitution in Sherman Hill.
I would love to see a way to let the random number generator know how rare a certain item should spawn.
From what I can gather, the "unofficial" max number of created liveries that will show up at one time is five. I have personally seen a max of four myself, and that was in the hump yard on SPG. However, it does seem that even less will usually show up in the manifest trains themselves. I can also attest to the fact that some seem to show up way more often than others. Rolling stock livery is interesting in that you can't really select for it, as you can for locos and such. On Series S at least, the game also runs more poorly as you increase the amount of liveries (and DLC), so for some players it might be best to limit this as much as possible.