Transferring mobile apps from iTunes (iPhone) to an external hard drive

Steps to perform this:

1. Navigate to the location you want to copy the files to and leave the window open in the Finder.

2. Create a smart playlist in iTunes by Option-Clicking the new playlist button in the bottom left of the main window.

3. Configure the playlist with the appropriate criteria, such as: {Last Played} {is before} {1/1/2008} or whatever you consider "Old." Click Ok

4. Select Edit, Select All and drag the items to the folder you opened in step 1. Wait for the copy to finish and you'll have all your old music in that folder.

5. To automate the process, use Automator and configure a new workflow similar to the following image:

6. Rig up the workflow you just created to run. Put it in the dock, use Crontab or run it at login.

This may not be the answer you are looking for but if you simple want to move you entire itunes library contents onto an external harddrive the simplest, best way in my opinion, is to move your entire ~/Music/iTunes folder onto the external drive then point iTunes to open the library in that location. Its as simple as closing iTunes, moving the folder, and then while opening iTunes again hold the option key (shift key for windows). It will then prompt you to choose which library you want iTunes to open. What you're really selecting is the iTunes library.xml file, but you can select your itunes folder and it will find the file.

If you want to experiment you can do the same thing while opening itunes and create a new library in a new location to play with.