The last book is an example of a book that is really about debugging, not about debugger implementation. This is the case for most books you will find with a title matching /.debug./.
Debugger knowledge seems to be scattered across the internet and language implementations. Also I never found a language implementation book that talks about how to make the implementation friendlier/compatible with writing a debugger.
This reminded me of the MaxMind story a few years ago, when they used some family farm in Kansas as the default location when they couldn't find a match for an IP.
If I recall correctly, it was a case of "we can tell this is in the US, but not where... so we return the center of the US with a _radius of error_ that encompasses the entire country"... and then a bunch of people who look at the location but not the radius. I seem to recall it happened with law enforcement more than once; which could lead to dangerous results.
And more generally there is "The Debugging Book" in python. https://www.debuggingbook.org/