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You can't sync progress between sideloaded books on a Kobo. As for me, yes, I usually remember where I left off (I switch between my two Kobos regularly). But then, I did the same when I used Kindles; I never used the whispersync. Finding my place manually was faster than switching wifi on and syncing. So it's always been habitual for me.
Some people just read different books on different devices.
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