Scott does tend to make his titles pretty cryptic. I could edit the LW version to include brief descriptions, leaving the version on my blog description-free for people who want a cleaner link list.
How much detail would be ideal? E.g., would 7 words per post be better than 20 words (since it'd be easier to skim such a list and spot quick keywords)?
I would say be flexible as some topics are much more complex than others. I've found that most summaries on this list have a good length.
I've put together a list of what I think are the best Yvain (Scott Alexander) posts for new readers, drawing from SlateStarCodex, LessWrong, and Scott's LiveJournal.
The list should make the most sense to people who start from the top and read through it in order, though skipping around is encouraged too. Rather than making a chronological list, I’ve tried to order things by a mix of "where do I think most people should start reading?" plus "sorting related posts together."
This is a work in progress; you’re invited to suggest things you’d add, remove, or shuffle around. Since many of the titles are a bit cryptic, I'm adding short descriptions. See my blog for a version without the descriptions.
I. Rationality and Rationalization
II. Probabilism
III. Science and Doubt
IV. Medicine, Therapy, and Human Enhancement
V. Introduction to Game Theory
VI. Promises and Principles
VII. Cognition and Association
VIII. Doing Good
IX. Liberty
X. Progress
XI. Social Justice
XII. Politicization
XIII. Competition and Cooperation
If you liked these posts and want more, I suggest browsing the SlateStarCodex archives.