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Forget about Mobi for Amazon. See though about Kindle Downloads on Smashwords.
Amazon perfectly converts epub2 to old mobi, KF8/AZW and KFX etc. They then deliver according to the customer's selected Kindle eInk model, or Fire, or app and according to if "Whispernet" (Mobile or WiFi) or "Transfer via PC" (which works with many phones, Tablets, MacOS and Linux, not just Windows) is selected.
Smashwords is a little more complicated than Amazon to upload to, but you can use the SAME epub2 as uploaded to Amazon. I put the Amazon ASIN *AND* the Smashwords "free" ISBN on the copyright page. Then that epub2 is distributed to Kobo, Tolino, Barnes&Noble, Apple etc and used for customer epub downloads. A Calibre created "Dual Mobi" from the epub2 works best for the Smashwords upload for Kindle Downloads as then ancient Kindles get the basic mobi and newer kindle owners can select "Publisher" which uses the AZW/KF8 part of the file. If you want PDF and LRF versions too on Smashwords you upload an MS Doc file also (not Docx). Their HTML and Mobireader (PDB) conversions from MS Doc are buggy, as are their mobi and epub, so uploading the epub2 direct and the "dual mobi" made from the epub2 (never direct from docx) in Calibre. This is the only use case I've found for the "so called" dual Mobi. I've tested it on DXG, Kindle Keyboard, Kindle Basic, PW3 and PW4 and it seems OK. It's not twice as big maybe because fonts and images are only in it once? I don't know how it works. You change the default Mobi output settings in Calibre to do it.
You can't upload a Dual Mobi to Amazon. The epub2 is best and gives the "Enhanced Typesetting" in KFX which must be a rendering feature not in AZW/KF8 rendering.
Don't use .doc for Calibre, but docx and only to make an epub2. Make all other conversions from the epub2.
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