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And... that is exactly why you have a problem.
Because you are supposed to use the Hotmail/Gmail/GMX/YahooMail account as a relay. Which means that calibre uploads the email to Gmail/whatever's servers, and gets them to send it on your behalf.
Using calibre itself as the mail server means calibre cannot prove it has the authority to send emails on behalf of that email address. Only Google can sign emails as having come from Google's servers.
...
tl;dr
If the email isn't in Sent Mail on the email provider's servers, you have definitely done at least one thing wrong, therefore your failure does not prove that Amazon has something against calibre.
Perhaps Amazon didn't used to verify that the email actually came from the email address it declares? I don't know one way or another (never bothered to find out) but it would be one way of explaining what has been seen here.
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