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I'd recommend buying from Kobo if possible, as it's generally cheaper (if you're in a country with price-matching) and the DRM is a lot easier to remove. Then use Amazon's "Send To Kindle" to send the drm-free epub version to your amazon account. Amazon then do a conversion to a suitable kindle format when you download to your kindle from your Amazon account.
But if buying from Amazon, you can still remove the DRM if you jump through hoops, but I don't know the details anymore, since I switched to buying from Kobo almost exclusively a year ago.
On hoop I do know is the one I use - have an old Kindle which can still download in a pre-KFX format from which the DRM can be easily removed.
I use calibre to track when I bought a book (date added to calibre), how much I paid, where I bought it from, the latter two being custom columns.
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