As for the wireless route, that's either a pure DIY approach with whatever transfer/sync/cloud solution you want in a script that you run with NM or KFMon (e.g., rsync, rclone, sftp, scp, ftp; you name it).
Or as an OPDS client against e.g., Calibre via KOReader.
Or as a Calibre Wireless Smart Device client, e.g., via KOReader or
@sherman's UNCaGED.
Note that with (most) wireless approaches, you lose much of the niceties involved in Calibre actually knowing that it's dealing with a Kobo, because it doesn't know that anymore.