Very well analysed. And I definitely agree about serendipity. That's a huge concern for me, and one reason why I haven't categorised the Founder's Library section yet. Splitting it into categories like the excellent http://www.gabrielweinberg.com/startupswiki/Ask_YC_Archive makes a lot of sense, but it almost completely takes away the serendipitous aspect, which is essential for startup advice.

The article you really should read is often not the one you're looking for. A system that makes it too easy to find what you think you need might paradoxically make it harder to stumble onto what you actually needed.

I also think that almost every great blogger who starts with the first use case ends up posting numerous timeless gems that get lost in the diary format. DaringFireball is, again, the obvious example.