"Fixed" sideloaded books and whispersync?

Hi all, long time reader but not posted much (if at all!). I did search for an answer to this but there is just so much about sideloading books!

Is it possible to use Calibre to fix a sideloaded book so it works with Goodreads AND sync your progress so I can read on my iPhone too?

I have been using a Kindle for a while, both with content purchased from Amazon and by emailing books purchased elsewhere to my Kindle email address. All works great, and I can read on my iPhone if I'm stuck somewhere without my Kindle.

I love being able to update my Goodreads account from my Kindle too, and of course this doesn't work with books that have been emailed because they appear as personal docs.

I've "fixed" sideloaded books before so they work with Goodreads, but then I have to manually plug my Kindle in and copy the file (or use the content server), which is fine, but then my reading location doesn't sync with my iPhone.

Is there any way to get both things working at the same time?