Solution is to install the Update Expired Podcasts script from Doug's Apple Scripts for iTunes, and then run this on a schedule using iCal.
First, create a new event. Simply double-click the proper time on the proper day and an hour-long event appears. Double-click the event, and the edit window appears. From here you can name your event, identify the location and duration (all day vs. timed), set repeat options and the target calendar if you maintain more than one (I don't).
Now for the fun part. Below the calendar option you'll see "Alarm." Clicking it reveals several options:
- None (kind of self-explanatory)
- Message (presents a dialog box on your Mac and iPhone/iPod touch if synced via MobileMe)
- Message with sound (same as above with plus a system sound)
- Email (send an email message to a given address)
- Open file (Open a file on your Mac)
- Run Script