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Amazon only syncs the books they have in your "library" on their site. I won't give them books via Send to Kindle out of principle. I did test it.
Kobo can sync books bought from Kobo. Calibre can "copy" reading position & status between Kobo models.
How many devices to you really read on? I have apps on two phones in use (one for house TFA and one for outdoors), three tablets, three laptops, a workstation and about 10 ereaders (One used to get azw3 from Amazon). But I read almost all novels on one Kobo Sage. If I need to read the same ebook on a different device it's faster to search than use sync, which needs two connections via WiFi to someone else's server.
Amazon Sync and the parasitic STK, which doesn't work to send Kindle format ebooks (available from Smashwords and PD sites), nor books with DRM, seems a lot to put up with vs every other aspect of a Kindle ereader inferior to a Kobo.
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