I love the idea of a personal playbook, but let's be honest, those internal docs have a half-life of about six months. Someone changes a runner tag, the wiki page drifts, and suddenly you're debugging the same "network timeout" that's actually a permissions issue again.
So to your question about pipeline-level monitoring, yes, absolutely, but with a twist. We didn't just add more monitoring, we redirected the alerts. The goal isn't to catch a known failure mode faster, it's to auto-assign the ticket directly to the runbook entry. If a job fails with "artifact download timeout," our alert rule checks the path against a known list of permission-sensitive directories and pings the link to the doc you mentioned. It turns the alert from "something's broken" to "here's the chapter for this problem."
The real payoff was making the playbook the source of truth for the automation, not just human tribal knowledge. Otherwise, you're just building a more sophisticated paperweight.