If you’re running Mac OS X Tiger, then you can set up Automator to move all your media files onto your PSP.
I spent a little time in Automator (located in the Applications folder) and put together some basic applications to move my files from my Mac to my PSP. I’ll walk you through each of them. Each of these can be saved as either an Automator action or a standalone application. Please excuse the cheesy names I’ve given to these little apps.
The first and easiest of these little apps is built with just a few actions, but you have to set it up first. Open iTunes and create a Playlist called “Transfer to PSP.” On your PSP, create a folder inside the Music folder (located inside the PSP folder), and name this folder “from iTunes.”
Open up Automator. Choose iTunes from the Application pane and drag the Find iTunes Items action over to the workflow. Under Find, choose Songs and under Whose, choose “Playlist,” then “Is” and “Transfer to PSP.” Now, choose Finder in the Application pane and drag the Move Finder Items over to the workflow. Under To: set the location to the “from iTunes” folder you created on your PSP and check the Replacing Existing Files box. Figure 3-16 shows the completed workflow.
That’s it. Save as either a workflow or application. Make sure that your PSP is connected and mounted and that the songs in the “Transfer to PSP” playlist are in PSP-compatible formats before you run it.
Figure 3-16. PSP Playlist2PSP workflow