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For instantaneous sending to Kindle, try Klip.me. The java bookmarklet makes sure you can use it on every modern browser, even those that have no send to Kindle extension available.
Clear out the personal documents part on your “Manage your contents and devices” page on Amazon.
PDF conversion is tricky. You could try installing Koreader after jailbreaking. This gives you loads of options (it takes virtually every file and makes it nicely readable). If for some reason you would rather like to use the built in reader (which isn't half as bad as on Kobo, and lets you add notes to annotations, not sure why Koreader still hasn’t implemented that option), try k2pdfopt (preferably use briss first, if you are dealing with uneven layout, e.g. for left and right binding or from scans). This lets you convert your larger page PDFs into page sizes that are better suited for smaller screens while retaining text flow and a comfortable font size.
Kindle does not support DRM'ed PDFs, so you may need to take care of that as well...
Good luck with your new gadget!
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