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What about on the spine? I agree it doesn't fit the cover, but right now the spine, from top to bottom, is [art], [title], [art], "LessWrong", [logo]. I wonder if it might make sense to either add a bit of whitespace at the top for the year, or at the bottom after the publisher info, such that it would look like "LessWrong ✵ 2019". This way it's subtle/understated, you don't have to change the title, but if, in 5-10 years' time, some of us have 2018-2027 on our bookshelves, and we want to find something we remember from 2023, we don't have to pull out each one to look at the back cover (or, gasp, be organized).
Also, what were the considerations regarding size? I know the size you picked was because you found it's what people are most likely to read, but I'm thinking that "book you might take to read in a coffeeshop or on a train" and "book you keep on your bookshelf at home" (which ozziegooen seemed to be making reference to above) are different aesthetics -- that is, I might assume the latter to be much heftier than the former, more like an academic journal than a pocketbook. Actually, I wonder then if it might make sense if it might make sense to abandon ship with the current book set -- to do the yearly wrap-ups as journal-style publications (that is, single-volume instead of five, larger, simpler cover -- you may not have seen it, but I'm thinking American Affairs-style), and then publish a set of best-all-time books (like Howie Lempel mentioned) in this nice size.