iPod love... or not

I have this folder in my iPod called "new stuff for testing". I use it to make sure that I listen to everything I put into iTunes at least one time. Everything gets dumped in there, and after it's been listened to it gets removed from the list next time I have the Pod hooked up to the computer.
In theory.
Unfortunately, this process breaks down in a few of spots:

1. Anytime the iPod locks up, which is way too often for my taste, it generally loses the information about what songs were played recently. It also does this when it runs out of power, sometimes.
2. Whatever my daughter has on her Shuffle*. She plugs it in daily, I plug mine in only every few days (or weeks, depending). If she's listened to one of her songs more recently than I have, it moves it up the list, ahead of the time when I know I was listening to my iPod. This is especially true of Green Day, which both she and my I-pod love.
3. Queen's "Radio Gaga". I'd swear I get rid of it, and the damned thing plays again. Why my iPod loves it, I have no idea, but it does, it really does.


* Not a problem anymore, since yesterday she dropped it while crossing the street and it got run over by a car. She's got a new one on her Christmas list, of course.