Amazing: an old Tiger app & its associated iTunes scripts (iTuneMyWalkman) still works in High Sierra. It lets you use iTunes to sync a playlist containing the term iTMW to a non-Apple device. First, attach the device (I use a USB drive) & mount it on the desktop. Open iTMW app & set the Preferences to suit the destination & source (which particular iTunes playlist you want to sync). Then add the various scripts from the downloaded zip file to the Scripts item under iTunes in either the user Library or the main Library.
Use the Scripts item on the iTunes menubar to control the process.