To be fair, those are specific people accompanying Zed which are far from being actual representatives of the whole order. They're probally some of the most powerful ones as well, so it's likely that they work in smaller numbers than the weaker acolytes. As an example, on Xayah and Rakan color story there was a fortrees with around 40 acolytes of the Order of Shadows serving as guards and the most notable shadow magic mentioned on the story was souls being infused into weapons, no shadow clones, limbs or anything(or at least if one them used it, it wasnt mentioned) . That was just one fortress and with the traning "ladder" mentioned by Odin on this post:
Zed is the master-- Kayn is his second in command. Lower level students mostly learn from mid tier students, mid tier learn from high tier, high tier from Kayn and Zed personally.
I would say that while their numbers are probally below 1.000, it's likely they still on the hundreds.
There was this one instance in a tavern that one of his followers did not know the concept of money because he was raised as a warrior from childhood and made threats to the bartender stuff for free food. Zed calmly orders the man to be set free. It does gives us insight the Kinkou order was one messed up organization.
I'm not sure I would word it as not having the concept of money. They're mercenaries, he should know about money and trade. I think it was more about feeling that he did more to Ionia than any other peasent who would pay them, and therefore should get free stuff as a kind of "thanks" from Ionians for even being alive. He feels like a war hero and a defender of the nation and thinks that everyone should treat him as above them for the role he plays.
Also did you mean Order of Shadows on that last line? I dont see how that event makes the Kinkou Order "messed up".