Help with purchased music and storage space for nano

I have a 2G Nano...I have purchased a few songs from itunes, but mostly transfered music from my CD's. The other day, I bought 2 songs from itunes and they will play in my library but not on my ipod. They show up, but when I go to them to play, it skips right over them. Any suggestions? I have updated several times and still no luck.
Also, I have a 2G, and I have 270 songs stored in my itunes library, and when I update (as I have several times in the past few days) it tells me that the disk space is full on my ipod, it is only using 1.01 G. Any suggestions?
Also, I have another question...if you resotre your ipod to factory settings, does it wipe out your songs in your library?
Thanks for the help...this is really bugging me.

See this article first.
iPod does not play content purchased from the iTMS.
Also, have a look at these articles.
<a href="<a href="http://docs.info.apple.com/article.html?artnum=60955">How much stuff will fit on my iPod?
My iTunes says my iPod is full but it isn't!.
"if you resotre your ipod to factory settings, does it wipe out your songs in your library"
Only on the iPod, it does not affect your iTunes library.

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