PC under XP Home- 2 session- 1 folder for music file

Hello
I have a PC under XP home.
Two users - One folder with music files. The folder "Itunes music" is on disk D and not under "documents ans settings" because it is too big for disk C.
Under each session my wife and me we have our database of iTunes.
It goes not very good. Sometimes we lose a lot of music and must import the folder one more time.
I don't understand why. In fact there is 20% of music who give problems.
Somebody have an explanation?
Best regards
PC Windows XP

...bit of an update since the last post i made:
I have now managed to update my iTunes to the latest version and have also installed the Nano onto my PC. I've even managed to trasnfer some music files onto the Nano also...
However, my problem lies with the iTunes library set up.
The 4thG 40g iPod i mentioned is used by a 35 year old hip hop fan who doesn't need to worry about Parental Guidance and until now has updated his iPod with ALL the songs that are in the library. Now i have a 11 year old daughter who likes typical 11 year stuff but i don't want to trawl thro 40g worth of music to find the stuff she can listen to .. whilst the 35 year old hip hop fan doesn't want to listen to tracks on random only to find he's got girls alound on his iPod!!
Is there anyway i can make seperate libraries for the 2 different iPod models? I have tried going into the iPod options when each of the iPods have been connected and have changed the path to the library but this hasn't helped so far...
again, any help would be truly appreciated...thank you

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