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Suggestion
Perhaps the general issue could be resolved with a "SYNC" (just as it works now) and a "Local SYNC" which manages the rest of your sideloaded resources -- But only with locally attached resources (No central KOBO servers). This implies that a Local Library - or My Library resource was available (Assume that it would have a local directory of Flat files & directories -- Like the KOBO has for side loaded books/ documents etc.
The Local SYNC would work directly with your KOBO e-reader (via direct connect & maybe wifi when the desktop can see the reader) and with your other device kobo reader SW only when those devices are visible to your desktop.
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