I agree with you that all the features of iPods can be confusing and there really isn't a lot of instruction included with them. I've found the only way to really know what you're doing is to play around with iTunes and see what all the different commands do. I did figure out a very quick way to play only my regular music during the non-holiday season (and vice versa) by doing this--a Smart Playlist.
Click on "File" on the top left. A menu should drop down. Then click on "New Smart Playlist" which is the second or third item in the list. A box should pop up on your screen with three different spaces in it. Go to those spaces. The first one (says "Artist" when the box pops up) you change with the dropdown arrow to "Genre." The second box can be changed to "Does not Contain" and then change the third box to "Holiday". That gives you a playlist that has everything but your Holiday music on it because when it makes the playlist, it excludes everything that says "Holiday" in the "Genre" column of iTunes. I call the list "Every day" and when I play it, no Christmas music comes up. You can do the same thing to make a Christmas playlist, by filling in the three boxes to say "Genre" "Contains" "Holiday." When you've hit the OK at the bottom, you'll get a box on the side that says "Untitled Playlist" and you just type in the name of your playlist, like "Christmas Music."
If any of the music doesn't say "Holiday" automatically when you put the cds in (I think my Charlie Brown cd said Jazz), you can change the genre listing in iTunes just by clicking on it and typing over it.
You can add more than one restriction for the playlist by clicking the little box with the + sign in it. That just gives you another row of boxes to further narrow down your playlist (for example if you're in the mood to hear only a couple of artists, you can create a new smart playlist, and then you can for example change the first row to "Artist" "is" "U2" then click the plus sign and change the second row that pops up to "Artist" "is" "Faith Hill" and so on and you'll get a playlist of only those artists you choose).
I'm not sure I'm explaining it well, but once you get in the right place and get the menu for the Smart Playlist, it's very self explanatory and easy to navigate. I hope this helps. Have fun playing around with it!
Just uncheck them in iTunes and sync your ipod. They won't be on your ipod. Then at Christmastime, you can create a playlist that includes all of your Christmas songs that you can list to.
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