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How can you keep your iTunes library "synced" to your USB Stick?

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I've copied my entire iTunes library to a 128GB USB stick which I use in the car. While I remain disappointed/dismayed there's no iPod integration with this techno car, I've found the USB drive works pretty well, only missing playlists and the ability to shuffle songs.

Anyway, is there a way to keep the USB drive in "sync" with iTunes?

What I'd like to be able to do is periodically take the USB drive from the car and plug it into my computer to have any new music I might have purchased be copied to USB drive.

I know in Finder I can recopy the entire iTunes library to the USB drive and then select the "do not overwrite" dialog when it starts trying to copy an existing file from the Mac to the drive.

However, I assume if I have a folder in iTunes called, for instance, "Elton John" which has a new subfolder with a new Album name "Diving Board", that new Folder/Album will not be copied without recopying all the other subfolders within the top-level folder?

Hope that makes sense. I'm just trying to figure out when I purchase new music in iTunes if there'a an easier way to update the USB drive than merely remembering what the new music is and copying that individually.
 
As mentioned above, rsync is a good option for doing directory syncs like this. On a Mac, you would use a command like

rsync --archive --verbose ~/Music/iTunes/iTunes\ Music/ /Volumes/USB/iTunes\ Music

Substitute USB with whatever your USB volume is named. Once you've got the syntax working like you want, you may want to add a "--delete" right after the --verbose so any files you delete out of your iTunes library also get removed from the flash drive.

A similar command line would work on Windows if you installed rsync. For Windows, another option is robocopy. This is part of Microsoft's Windows Resource Kit that is a free download. It can do a similar "sync only the changes" process that is implemented by rsync.
 
A bit of study of the rsync command might be in order. This is a very common and popular Unix utility. Command line. Am certain its available for Windows too but its included on Mac. Or maybe I got it in Xcode?

I was going to suggest the exact same thing. Forget loading another application when you can just use the terminal/command line to copy new files within a directory.
 
I am not home, so I can't get the name of it, but my Audis have SD card slots, so I used an app that would recognize a specific SD card when inserted, then sync the iTunes folders or playlists that you specify. It's what I use on my USB stick now in the Model S -- insert it, and it syncs just like it's an iPod. On windows it ran in the system try and popped up when you inserted the configured media.
 
I am not home, so I can't get the name of it, but my Audis have SD card slots, so I used an app that would recognize a specific SD card when inserted, then sync the iTunes folders or playlists that you specify. It's what I use on my USB stick now in the Model S -- insert it, and it syncs just like it's an iPod. On windows it ran in the system try and popped up when you inserted the configured media.

The software I use is called iTunes Agent, and it looks like in '11 it got renamed to notpod: Notpod - Portable entertainment manager

here's another software, though it's a tad more limited. iTunes Sync Binary Fortress Software