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If you have the newer Kindle (the K3) it will read PDF files without conversion. If you have an older Kindle you will have to convert them yourself with Calibre, or you can use Amazon's service where you email them the file(s) and they do the conversion for you.
As to which of your books are DRM'd, it's impossible for us to tell. A good guess is if you got them for free, they're probably not. If you paid for them, they probably are, but that's not always true. The other way to find out for sure is to try to convert them with Calibre. It will convert non-DRM'd books, if they have DRM the conversion will fail.
The DRM issue begs the question, are you transitioning from a different reader? What is the format of your extensive ebook library? The answer to that question might help determine which reader is best for you.
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