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Forget about Calibre at all. It is a very good library management tool, but not so much for conversion. Not only that, PDF is the worst format to start from. A lot of repair/rework will be required if the source is PDF.
Second, also forget about DRM. It will be very expensive to achieve and is broken within a second. Not worth the effort. If you have a book worth reading and not too heavily priced, people will buy it.
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