I am on a 10 year old Kindle and looking to replace it but most of my ebooks are from Amazon. Would it be seamless to transfer my books to Kobo via Calibre or some other software or it will be pain in the butt?
You can check beforehand by installing Calibre with the de-DRM plugin and transferring a few books: Once they are on Calibre you are good to go.
One thing I only learned today is that you can set up web sync from Calibre to Kobo [0], [1], but just plugging in to sync has been working fine for me.
For the initial sync, it used to be you could directly de-DRM your whole collection from the storage of the kindle desktop app. At some point the desktop app was using a DRM that had not been broken: I do not know if this is still the case, or if there is another way to download everything from your account.
[0]: https://news.ycombinator.com/item?id=39996455 [1]: https://brandonjkessler.com/technology/2021/04/26/setup-kobo...