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no other reader that I have prompts to connect or not
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Really? Every device does this, even the $1000 "smart" phone. If it didn't ask, as JSWolf said you could probably not read while charging. This has technical reasons. A filesystem can only be mounted by one machine at the time; while you read it's mounted by your reader; while it's in usb storage, it's [assumed to be] mounted by your computer and the reader must not access it during that time, otherwise you get data corruption.
A "read while charging" feature under these circumstances would involve the reader keeping a copy of the current book in memory (and then you could not switch books while charging).
It's possible to upload files through wifi, if you have a FTP server running. Unfortunately the Kobo does not know about those uploads and does not update its database. Maybe it would work for an external SD card which you can pop in/out while the device is running... and you can communicate this SD switch to nickel through the hardware status.