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This would probably require a lot of front loaded work in your case, but if you need to train a boat load of people with very few (or zero) trainers, my favorite way to do it is (Atlassian’s Atlaskit Onboarding/Spotlight components)[https://atlaskit.atlassian.com/packages/design-system/onboar...]

Interesting... My to-go solution for this would be a detailed wiki page with screenshots, and link to that from a bunch of places. But I guess that's not an ideal solution really.

What do you use for the wiki?

World of Warcraft

we use little floating checklist from userpilot.com