OK great. I guess u plug in the iPod, then when ready, run getCals.
If u folks (advance users) want to automate the whole process, this is how:
Schedule getCals run(s), have it deposit the calendar file into your HD (choose any loc).
Download my iNotes util (click my Winscript sig), this will sit there and waits for u to plug in the iPod (whenever), and graps the the calendar (and other files like notes) from HD -> iPod. Warning: I cannot provide support for this util, u have access to the source.