This has been going on for some time.

Question

this is getting very frusturating. i've tried everything, even "restoring iPod to factory settings"
I put a CD in that I would like on my iPod, i import it to my iTunes, but then it takes another CD out of my iTunes & off my iPod!
My iPod always has around 50 songs due to this. I don't know why it does that, I have more than 80% of its free space left!
My sister got the new video iPod over the summer, but it didn't work on our computer, thats when this all started.
I've also tried downloading the new version of iTunes, but it won't let me!
I'm getting very irritated, please help.

Answer 1

If you are really running Windows 98 you can't be running iTunes.
If you are importing songs from your CD into your iTunes library, syncing them to your iPod, and then deleting them from your iTunes library it will always remove the songs the next time you connect your iPod. If you don't want to do this set up your iPod to manually manage your music and then manually drag songs to your iPod.
To set it to manually manage your music connect it to your computer. In iTunes select your iPod under the Devices section on the frame to the far left of your screen. Move to the right and select the Summary Tab. Scroll down and you will see an Options section. Tick the box for manually manage your music then click Apply.
You will need to manually eject your iPod when you are through dragging songs to it.