idk seems like an interesting topic, especially for boomers who've had years to find stuff.
The most expensive one I own is a hardcover of The Killing Star that sells for like $300 on amazon.
I got it for $30 last year 
Most expensive book you own?
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911roofer
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talk about books or smth idk
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None really, just some hardcover sets that go for ~$90. I almost got a used first edition hardcover of Gravity's Rainbow off Amazon for like $200 that I suspect was worth $400 or more, but the seller took it off after I bought it (maybe realized it was worth more?).
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