GMail's maximum attachment size is currently, I believe, 25MB.
I think the only solution is to use a cloud based method (outside of Calibre I would think, but I have no experience with Calibre and the cloud). Given you are using GMail, among those is if you compose an email from the GMail webpage for your Gmail account it gives the option for attachments to be made from Drive up to a limit of, I believe, 25GB or the size of one's account whichever is the lesser.
However, how you get to that from a Kindle I have no idea, but it would seem to me that as long as the cable is long enough to go between the PC and wherever the Kindle is then that would seem by far the easiest to me.
Last edited by AnotherCat; 11-05-2013 at 04:06 PM.
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