Looking for a way to automatically resend all updated files

Hello,

I was wondering if it's possible to first compare the on-device "Date" column to the Calibre "Modified" column, and then if the Calibre file is more current than the file on the device, delete the device's book and upload the changed Calibre book. I have a library consisting of hundreds of files, and sometimes the metadata needs updating, or other changes have been made that require a reupload. Is it possible to do this without manual intervention for every file?

Thanks for any help you can provide.