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Some versions of VNC have a (windows) file transfer feature.
I am with Eschwartz. Don't mix OS
Why not VNC into your 'server' (assumes it is NOT Headless) and do Calibre there and also run the Calibre server / Wireless device connection (for CC Users) on that box.
All Library admin and GUI would be done via the 'remote' (Any PC with a VNC Client)
You would drop the files into the Auto-Add folder (VNC file transfer OR FTP...)
then tune the metadata
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