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Kindle's Send-to-Kindle service is a joke. If the EPUB doesn't have the ISO setting, then it defaults to ISO-8859-1 which then messes up special characters like צהו and such. Also, their EPUB conversion is terrible compared to the one in Calibre. I gave up on that service and side load via Calibre to Kindle from now on for me and my girlfriend.
As to my mom, I have been struggling with the same issue as the OP as she is not very techy person and even side loading is way to complicated for her and she lives too far away for me to do side loading for her.
So I was looking at some options and it seems that Pocketbook has a Send-to-Pocketbook service which you can email your Epub (just like Amazon) but AFAIK they do not make any conversion but just simply redirects the EPUB file to the Pocketbook in question. I think Pocketbooks also have Dropbox support which would allow you to control what books she sees on her device.
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