I'm tired of always having to click "Autofill" in iTunes to put new songs and podcasts on my second generation iPod shuffle so I'm looking for a way to automate this with a keyboard shortcut, AppleScript, etc.
According to Apple's iPod shuffle FAQ, what I want to do isn't possible. . .
How do I make Autofill automatic—like how automatic syncing works on other iPods?
Autofill actually requires some action. You can manually click on Autofill each time you insert iPod shuffle, or you can use the "Keep this iPod in the source list" option to click Autofill any time and then connect iPod shuffle.
. . . but surely there is some way to improve my current workflow, which is to plug in my iPod shuffle, click it in the device list, and then click "Autofill". Any suggestions?
p.s. Apparently that "Keep this iPod in the source list" option went away with iTunes 7; I don't have any such option in iTunes 10.