I have an iPod for quite a long time now and I have never quite got to grips with iTunes. I pretty much worked out how to put songs on by using playlists. What I can't understand is why you can't select lots of songs and drive the ball across. You could do, but if you've got 30 albums, you don't want that all in the same playlist. I want to be able to have individual folders. What I can't seem to do is manually drag it across the various songs out of lots of others. If I hit control and click I can select numerous ones like that but that is time-consuming. I really don't like iTunes, in fact I think it is an absolute pile of crap

I have an ipod nano as does my wife (shuffle) and youngest daughter (an expensive one) too. Funy thing is my older daughter (25) never took the interest and never wanted one.

YOU probably know more about using it then I do and my daughter knows way more about it then me or my wife. I do know it was aggrevating was that we couldn't set up two individual accounts on the same computer for my wife and I. It forced us to share an account and that's a pain because we both have different tastes in music. But its all lumped together under one account.
I started out with a lesser known MP3 player as I myself wanted to avoid apple and itunes . So, I started off with MSN Music purchased a ton and later found out the MP3 player was hard to use and I literally couldn't get my music to play on it. So, I went with a NANO (I think they got it for me for fathers day or something). Now, ask me how often I actually use it? I am probably more apt to sit at my computer and open my music and play it off the computer speakers...

When my daughter comes home after finals (another week), I'll have her take a look at your message and reply if she understands what you need to know..

I have finally sussed it out. I have been making playlists. The one huge drawback about doing it this way is that you can't actually drag over a selection of songs and select them all at once, you have to select them one at a time. Because of this, it could take a long time if you have a lot of songs. If this is indeed the case, I think this is a serious design flaw in the software as you should have the choice to do it.

have you tried windows media player