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I buy my books direct from self-published authors or from publishers that support DRM free formats. Publishers like O'Reilly, Pragmatic Publishers, No Starch Press, Manning, Apress and imprints under InformIT have been making ebooks available in multiple DRM-free formats for years now.
I hope one day Amazon, Kobo and Apple will push other publishers to take the same route, much like iTunes Music went DRM-free years ago.
Compared to Send to Kindle, Apple has the best app for sideloading books. Drop ePubs on iBooks and sync.
For eReaders I sideload books by syncing them with a command line script I wrote. O'Reilly and Pragmatic Programmers update my purchased books in Dropbox, which i then sync to my Kobo.
Calibre is very capable, but the UI hurts my eyes. I haven't bothered investing the time to figure it out.
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