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I've been exclusively using a Chromebook for the last year while deliberating on what to get as far as a desktop/laptop goes (and when lol), and quite happily use calibre on it.
Yes there are some challenges related to how ChromeOS shares USB connected devices between the native ChromeOS environment and the emulated Linux subsystem (aka Linux development environment, or crostini), but the majority of those were resolved with a recent calibre change allowing the mount of a folder to specify an eReader type (in my case a Kobo).
I've happily run calibre from the official Linux downloads at version from 5.44 to 8.04. No issues with plugins including DeACSM, DEDRM and OverDrive Libby. Also no issues with either the built in Calibre WEB server or the wireless device driver.
Sure there are always a few idiosyncrasies but I'm happy with it.
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