Time is a flat circle, eh?
But all kidding aside, web directories should be much more powerful now than in the 90s. Websites have RSS, and directory websites should be able to automatically monitor things like uptime, and leverage RSS to preview a site's most recent post.
I've considered maintaining my own directory on my personal website (a one-way webring if you will), but always stopped because the sites I linked to either died, or were acquired and became something very different.
Well, we have awesome-* in GitHub now. Unfortunately RSS seems to still be hit-or-miss.
Do you mind clarifying what you're referring to?