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I advocate rotating roles, and having an operational doc, the trick being people have to repeatedly read and update the operational doc to fill the role they have just been assigned.

Mandating the doc stays up to date when noone is actively using it is an exercise in time wasting

The problem you are facing is the weakness of having individual specialists. The problem is not the doc maintenance but organisational

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How do you manage rare events in such a setup? For example, how to restore a database from backup is valuable knowledge that should be documented somewhere so you don't have to make it up as you go along. At the same time, in (almost) every place I've ever worked at this was not required very often.

This seems like something chaos engineering and/or a proper ops team with regular disaster exercises would be able to pick up, but (like you mention) in most startups those seem to have very low organisational priority.

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