Those examples would definitely be interesting to read. I'm one of the many people who feels search results have gotten worse, but since I don't have any actual saved search results from 10 years ago it's really hard to say if I'm right or misremembering. Some concrete examples of what Google2000 looked like might be good for jogging the memory.
One example category does come to mind, which is a frequent pet peeve: lyrics searches. They definitely return sort of crappy results currently, but I can't say for sure what they returned in 2000, since I didn't save any results.
Examples:
Imo [joy division walked in line lyrics] should return a page like http://www.joydiv.org/shadowplay/joyd/walkedline.html. Instead it returns a bunch of sites like lyricsfreak.com, sing365.com, lyricsdepot.com, metrolyrics.com, etc.
The case is even stronger if there's actually an official site for the musician with official lyrics. An example of that: [vnv nation fragments lyrics] should return http://www.vnvnation.com/Webfiles/lyrics/fragments.htm, but instead it again returns the usual lyrics-site suspects.
I think my recollection is that I used to get fan sites more than lyrics aggregators in 2000. That might be more due to web changes than Google changes, admittedly, since many of these lyrics aggregators didn't exist in 2000, and hobbyist fan sites may have been more vibrant. The fact that the same lyrics-aggregator sites dominate for almost all the searches seems weird, though; it seems that basically all lyrics searches return "big lyrics site", rather than trying to retrieve a site specializing in the band I searched for.