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1) Is there a way to force sync Overdrive with my KA1? (short of signing out and signing back in as I've been doing?)
No, but a normal sync should work just by hitting the sync button. You shouldn't need to sign in and out of anything.
2) How long does the KA1 usually take to notice a new library loan?
In my experience a few minutes.
3) Are there books that can't be loaned onto the KA1 for some DRM reason?
Not for DRM reasons, but the Kobo store needs to have the same edition of the ebooks you're borrowing. Not just the same title.
4) Is the problem I am running into avoided by doing all my Overdrive borrowing from the KA1 instead of using my desktop web browser as I usually do?
The more you do from the device itself the better as far as i can tell.
Do make sure you're running the current firmware, which is at least 4.3xx but preferably 4.4xx
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