One reason I've avoided blogging was the way all blogs seem to be organized. They gather all your information in a sort of "stream of consciousness" format, regardless of which entries are infrequent but carefully crafted commentary and which are just short notes. Ideally, I might like my site to be more like a magazine, with the best essays highlighted front and center on the home page. Also, all content should be organized in a table of contents by topic, not by date posted! The latest posts could be shown in a "what's new" section. My old home page and my writing page tried to accomplish this to a degree.
If someone discovers a blog a year or two after it's been around, they have no idea what the best essays were from the past. I think this is a shortcoming of any blog that posts infrequent but substantial essays (like tecznotes's book reviews or Aaron Swartz's essays). It's as if instead of a book being organized by chapters, it was laid out in the order the author sat down and wrote each chapter!
Actually, though, most blogs I read work fine in the conventional blog format. They deliver a consistent stream of tidbits or excerpts (like Kottke or Brad DeLong). Each entry has about the same significance level. For those blogs, I can't think of any good way to help people dig into past blog entries, without spending way more time on organizing at the expense of content generation. Unfortunately or not, a reader might as well jump into the blog at any point and ignore past entries. The frustrating effect of this is to obscure a significant segment of the internet behind the serendipity of the search box!
It's likely none of this matters, and I won't be posting many long essays, aside from maybe a few I've sent to friends in the past. Maybe I won't even post anything that deserves to be highlighted beyond the day it was posted! While waiting for the conventional blog format to evolve, maybe my thoughts have evolved into handy blog-formatted bits.