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stepping back a little
you have some DRM free epubs - yes?
you want to read those on kindle but you get errors with send to, and with copy via USB
how about you try with a new clean install of current calibre on laptop i.e. you wipe all the calibre config stuff in app data before installing, then you do a conversion to mobi using all default calibre settings. see if you can send that, and also see if you can read that conversion in Kindle for PC...
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