It works!
With the latest ChromeOS (74, as of this writing), it's easy to share folders with the linux container (from 'Files', right-click the folder and select 'share with linux'). If I plug in my kindle, it shows up in the linux container as /mnt/chromeos/removable/Kindle.
I had a quick try with Calibre, and it looks like it's possible to use the 'Folder Device Interface' plugin to access it. It's not quite as automagic as just plugging in an USB device, but it works reasonably well.
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