Which is more indicative of a scholar's quality: The quality of their first book or the quality of the latest book? Why?
Only asking about book-focused scholars here. I know that many people focus on writing articles.
Yes, but also because the first book comes from years of research with lots of time. Most supervisors aren't all that involved anyway. And in some respects, the early work could be considered more 'independent' because you have a smaller network of people to get feedback from.
Second books are often weaker because people put something out quickly under the demands of teaching at the same time, starting family, etc.
More broadly, this is a s*lly question because it varies so much by individual circumstance. The only way to judge any scholar is to look at the entire body of work and then analyze from there.