Manage external USB drive in iTunes as if it was an iPod

Question

Is there any way to manage an external USB drive in iTunes as if it was an iPod? Specifically, have it appear as a device in iTunes, and be able to specify which playlists, etc., should be synced to it.

The use case is managing a USB stick that I use in my car. Currently, I have a smart playlist that I want synced to it, and every time I want to make an update, I delete all the files on the USB stick and then copy the playlist over, which is far from ideal.

Answer 1

In the end I wrote my own solution for this, FlashTunes, which is now available on the app store.

It'll keep track of everything for you automatically, so you can just set it up once, and then every time you reconnect the device it'll figure out what to sync automatically, much like iTunes does for iPods.

See the demo here.

Answer 2

The venerable Doug’s Scripts for iTunes has many AppleScript to export and export/convert songs in case you wanted them to be MP3 or re-encoded when you export them. Also available is an inexpensive app to automate this even better than the scripts:

• https://dougscripts.com/apps/m3unifyapp.php