Up front, yeah. Once done, you can mix and match at will, which was the goal. After Christmas, unchecking the Christmas playlist makes the seasonal stuff go away. As cumbersome as it seems, it went quickly once the lightbulb went on in my head. And believe me, it's much, much quicker than doing it all manually (by cherrypicking music from the library and the iPod itself). I've done that too. Ugh!
I don't know. I realize that it may be easier with a plugin for something like Winamp, where the philosophy is not overbearingly restrictive (as it is with Apple). But the practical fact is that everything is already organized under iTunes, and going off the reservation, as I called it, brings in the unknown *and* a good bit of work too, reinventing the wheel (i.e., piling up the music to be sent to the device). As the man said, you pays your money, and you takes your choice.