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Hi, I am the author of that. Would you say the depiction in the article is more-or-less accurate? I am asking as I wrote this purely from an outside/theoretical perspective.
It's very true for some things, and not for others. There's information asymmetry in both directions, things site owners know that Google doesn't, and things that Google knows that site owners don't.

The summary of the history seems pretty accurate to my perception of it, but I don't think it's hopeless from here. :)

My life is going from using a Google that used to give me useful results to one where "tar up website" returns the top result:

"Deep-sea ice crystals stymie Gulf oil leak fix - Yahoo! News 8 May 2010 ... thick blobs of tar began washing up on Alabama's white sand beaches. ... platform at the Deep Sea Horizon oil spill site in the Gulf"

At least a result from 4 days ago is an improvement on when I'd get usenet or mailing list results from 1999-2004 whenever I searched for anything linuxy.

:/

Tell us more!
I wish I could. :)

All of the fascinating things about signals are confidential for all of the reasons listed in the article, and Google has been sued so many times by sites that think they should rank better than they do that I can't really give examples.

I think it's safe to say though that there are a lot of people worried about and thinking hard about what the web is turning into and how to rank it appropriately.

Most of the content is no longer written by devoted hobbyists, people no longer link as often to things they like, and much of the content on the front pages of reddit, digg (and sometimes even hackernews) was put there by people trying to make your search results worse.

I feel like you missed listing a big change: with the rise of UGC sites, the boosting of results of anything on an "important" domain doesn't seem valid anymore. Just because something is on twitter.com doesn't mean it's highly relevant, since anyone could've posted it. But it's fairly easy to google bomb someone's name by just registering a Twitter account and listing their name as owning it.

Similarly, stackoverflow.com doesn't have very good answers for a number of technical topics, but it's often on the first 10 hits, even when the answers are useless and there's much better answers ranked lower (like project mailing list archives).

I think that a mailing list only search engine done well and broadly would be a very useful technical resource. Much of the internet, at least for SysAdmins and Systems Programmers still happens on mailing lists.
Yeah, I often find myself wanting an "exclude answers sites and wikis that aren't Wikipedia" checkbox.
The days of a central search engine 'indexing' the Web are nearing an end---indeed, it's already over, people just don't realize it yet. New material now appears much faster than it can possibly be indexed, and unless Google figures out a way to beat Einstein, it's only going to fall further and further behind. People will discover relevant material through their network, in a massively parallel fashion. Everyone will be their own Google.