Updating iPod Overwrite Question

It seems that when I can update "Pamela's iPod",with something new, it writes over what's already on the iPod, so I have to update everything from the beginning. Shouldn't you be able to update the iPod without erasing what's already there?
Also, is there a device that will play both .aa and mp3 files that is manufactured for Windows? I like the concept of the iPod, but it really is lousy to get it to work.
One more question. Do I really need Microsoft's Service 2 pack update?
Thanks!

007: Thanks for replying. I'm having all sorts of problems getting music copied to Pamela's iPod. Audible books works just fine. The problem I spoke about above is that I can't seem to be able to add, for example, a song to my iPod without adding all the other stuff already on it again. If I don't add my entire Library along with the single song, everything on my iPod is gone except for the newly added song.
Also, some folks have said for me to drag and drop. This doesn't work either. Last night I thought that I copied to my iPod an entire album (I imported from the CD and then clicked from the file drop-down menu, Update) and when I went to play the album this morning, only the first song played.
If you could walk me through this process, I'd sure appreciate it. Love your movies--
Thanks!
Pam

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    GamingChamp wrote:
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    JPBentley wrote:
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