If those users aren't reading the error dialogs anyways, why do the error dialogs need to pander to those users? I wonder if the "make it dumb enough for every user to understand" approach leads to user comprehension plateauing prematurely.
You would programmatically build the self help tutorial like a ui test (use a test browser and it would be like cypress/selenium). You would write a script, (ai) text to speech, and you could even respond to user input for branching.
These would be, de facto, your acceptance test suite and your tutorials will flag when they break on new ui developments, helping to keep them up to date
Even that isn’t a given. I’ve seen banks using emoji in their notifications. Companies are using ML to predict which emoji to change your text to. There are emoji domain names. Etcetera.