How long before I can assume the update failed?

You know that page that says:

Wrapping up installation… Please do not interrupt.
This can take a few more minutes, but we are almost there.

Well, that page has been up for at least a half hour. At what point should I just ignore the “please do not interrupt” part, and assume that the install is b0rked?

That’s happened to me a few times. I waited about an hour and then I just rebooted the RPi and it was successful.

You might try that and see if the update worked for you.

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Sometimes a manual refresh of the page works too, and occasionally I have had the device change IPs – doesn’t hurt to check if that is the case.

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Unplug the RPi and then plug it back in. That frequently works.