I am having a hard time syncing content across devices, specifically personal docs. I want to be able to view the same Docs whether I am on my PC, Fire Tablet or iPhone. Has anyone successfully synced personal Docs?
yes, by using the Send to Kindle app or using your Send to Kindle email address, but not for Kindle for PC/Mac or the Cloud Reader as those do not officially support anything other than Books purchased from Amazon. Kindle for PC does have a import function for pdfs but those will not sync to your account.
Unless you added the outside books to your Amazon library, you have to manually provide for backups and restores to new devices. Personal documents are just that: personal and Amazon doesn't bother with them unless you convert them to Amazon;'s format.
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Does this mean that ebooks obtained from Book Funnel or other non-Amazon entities can not be sent to my fire?
My kindle is slowly becoming outdated and I have just gotten a new Fire HD8,. I find the amazon (.mobi ) files were transferred but not the non-amazon book files (.doc).
no, not if you used the Send to Kindle app or the Send to Kindle email option. And those books from other sources would be available under the Docs app. I did that with all my Humble Book Bundles, free books from Tor and Baen books.