Learning from other people's debugging stories/nightmares is at the heart of Debugg. My basic understanding of this is if you've read that story, you're less likely to feel lost when you encounter a similar situation.
So I started a blog series on DEV sharing people's debugging stories and asking people to share their own in the comments (or otherwise). I'm also using this as an opportunity to gather scenarios on which to base Debugg's Problem statement on, so that I can increase the amount and variety of Problems people can solve on their.
Hopefully, it works out well.