Thanks Joe. I think the difference you point out only strengthen analogy, and which I tried to colorfully explore in the original post, but expand here because it is interesting.
«It is not as obvious that software is also a set of assertions about the world - and it's not as easy to determine which assertions about the world the software depends on.»
I like that definition: "Software is a set of assertions about the world". It may be less obvious than an Encyclopedia, but again, perhaps that only makes it a better analogy.
«An encyclopedia is a static list of supposed facts and its change is somewhat predictable by in terms of how our understanding of the world changes.»
Ah. This is where Wikipedia actually strengthens the analogy. An Encyclopedia has always been loosely hyperlinked with cross-references. Entire complex webs of assumptions and assertions about the state of the world. Refactors of Encyclopedia content always could have interesting complex relationships with other content.
Certainly there is an extent to which Encyclopedias are known to predictably change: new elected officials each cycle, for example. But there is still plenty of unpredictable changes: new red letter days in history, new evolutionary scientific shifts in consensus, new lenses in which a culture views itself.
An example of the lattermost, in that yellowed 70s Encyclopedia you could still spot fragments in the process of being excised of what we now consider to be racist views of culture and cultural history. That among other things was a source of fascination to this teen in the 90s.
The often unspoken truth is that as much as Encyclopedias try very hard to be objective, they are still a product of their culture. (So too do we often want to think that Software is objective and nothing but mathematical assertions about facts about our world, but here too they are products of our [corporate] cultures and moored in ways both obvious and not obvious to the culture that built them.)
Wikipedia shows us that complexity of Encyclopedias much more directly, but those bones were always there in Encyclopedias even when we couldn't see them. A link to click is much faster than shuffling between volumes of an encyclopedia to follow cross-references, but the cross-references have always been necessary to build up a view of the assertions about the world.
More interestingly, Wikipedia strives to give a better, more transparent view, into the cultural biases of its contents; all of the [citation needed] tags and "More Research Required" templates and Talk pages of endless discussion. The novelty here is that they've opened up all of that to the common user, but the essence of that has always been in Encyclopedias, just locked away by the librarians and researchers in their own notes.