Doesn't seem that difficult. Raiding guilds in Everquest and WoW pulled this off for years with 40 players and more.
Speaking personally, until very recently my regular raiding guild only had about 26 or so raiders who could show up every night (and another 3 or 4 who could show up for 1 or 2 of the nights). And yet we still managed to clear 8/8H.
I'm not proud of those days, but it did help me realize the key to managing any large group of people: make it feel like work, make everyone believe that it is a job and not a leisure activity so that you feel obligated to stay despite a complete lack of anything resembling fun.
So, yeah, I can imagine this actually happening. If you could do it with EverQuest, you can probably manage to achieve it with Minecraft.