You want a way for calibre to login to every ereader store out there, parse the list of purchases, index the download links and download your books for you?
Not happening.
Maybe if someone wrote a plugin and was willing to constantly update it as websites get updated. People already have their hands full keeping track of the metadata sources, and those have no alternative.
Automatic synchronization is not on anyone's TODO list.
ebooks are not deleted on the Kindle until you choose to delete them. I don't know why the Tolino would...
Either way, as long as you add them while they
are on the device, calibre won't care.
All you need are the new books anyway -- the ones that weren't added to calibre yet.