Yes, good point that this form of communication is prone to ambiguity in the ambiguity (poorly labeled links). And I'd agree with you that it's a bad thing for technical writing and for (many) uses in PM *posts*. But, that's why I specifically talk about the Chatterbox, rather than linking in general - it's a conversational pattern.
Your post also highlights two other issues. First is the post modern meta-comment thing: you fool us by making both your good and bad examples link to the same page since what you are emphasizing is the bad anchor caption, not the bad target. But this in itself is part of the conversational pattern - that the form of the link becomes an additional communication channel in itself and is available for use as irony or emphasis just as other sorts of communication markers are. When someone in the Chatterbox says "that's logical" and links the word logical to the Amazon.com listing for the novel _Catch_22_, they are using the contrast in the form and contents of the link as communication.
Speaking as an author (See the hat? It says "Goal in life: annoy editors", which can be a problem since I've also worn the editor hat numerous times), I happen to like having multiple communication channels available (depending on the purpose of the discourse, natch).
The other thing your post highlights is that different forms of communication are appropriate for different forms of discourse. We could imagine a time-scale of discourse with a college seminar at one end, blog/wiki/PM post in the middle, and the Chatterbox at the other end and a verbal conversation even farther at that end. In the seminar, the prof can say "Next let's discuss the novel Catch 22" and expect that with the week's time lag till the next seminar, the students will have read the novel and "inserted" its contents into the ongoing conversation of the seminar. In a blog or wiki or PM post, a reference to the novel might serve as context-setter for those who know it and as a curiousity-tweaker for those who don't. For references shorter than a novel - say an online magazine article- the blog author might even expect that some readers will follow the link and read it (unless it's Slashdot :-)), then with a time lag, return to the blog and contribute to the discussion. In an ordinary verbal conversation, if someone mentions a short magazine article, the conversation doesn't pause while everyone goes and reads it - too much time lag. But in the Chatterbox, that sort of time lag *is* possible - people do go off and read the links and return to the conversation to discuss them.
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Certainly the chatterbox is more casual, but it's rarer to have too much context for links than not enough. Consider the case where someone inadvertently links to something potentially offensive (or at least not safe for the environments of certain other people) without warning.
I think it's better to err, if it is at all erring, on the side of more context, even in casual situations.
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