this post was submitted on 29 Nov 2023
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I'm kind of surprised if Kindle is the only one that has that feature. Did you check the competitors?
You can use Send to Kindle email method to upload files as well. It works with Calibre. The page I linked has "Other ways to send" section which lists all the methods and how to use them. The web app has 200MB file size limit, the rest are limited to 50MB per file.
Also, while Send to Kindle supports EPUB, Kindle does not: Send to Kindle will convert the files to a Kindle's own file format. This conversion can sometimes mess things up, but they have been improving it since they added EPUB support last year. You might want to try out the Kindle iOS and Desktop apps before spending money on the actual device, and test how Send to Kindle works.
I was looking into kobo, but some reddit posts said that sideloaded books dont sync. It was a little older so I just wanted to see if anything had changed.
Thanks for all the information.