If you have firmware 3.3, the sychronization of personal documents should work naturally with no hoops to jump though (Bullet 3):
Dear Kindle Customer,
As a past user of the Kindle Personal Documents Service, we are pleased to let you know about some improvements:
• Your documents are now automatically archived in your Kindle library (you can control this from the Manage Your Kindle page at www.amazon.com/manageyourkindle).
• Archived documents can be re-downloaded from your archive to the all-new Kindle and Kindle Touch devices, as well as Kindle Keyboard (Kindle 3rd Generation--requires the latest software update v3.3 from www.amazon.com/kindlesoftwareupdates) – you will be able to find and download your documents from any of these devices that are registered to your account.
• Now (just as with Kindle books) Whispersync automatically synchronizes your last page read, bookmarks and annotations for your documents (with the exception of PDFs) across devices.
We expect to extend these features to Kindle Fire and Kindle apps (such as Kindle Cloud Reader, Kindle for Android, Kindle for iPhone, Kindle for PC, and Kindle for Mac) in the coming months.
I'm not sure if they've rolled that out to the mobile apps yet, but if not, I'm sure it won't be long.
So technically, calibre's behind the scenes ASIN-faking could actually hinder
that new process.
or e-mail to transfer to the Kindle - Is that supposed to work?
Previously, before the new personal document archiving service, the old method of syncing Last Page Read would definitely be broken by emailing the book to your Kindle.
A very large thread discussing the old method(s).