Authorizing and purchased music

I am completely struggling; please help. I have had two iPods (one a replacement on a warranty). The second I got last November.
Since the first iPod I've had two computers. My account says I have one (current, I guess) authorized. However, some music purchased some time ago apparently isn't on my iPod. For example, one playlist shows 315 songs in my music library. The playlist on my iPod shows about 260. I don't know how to begin to straighten this out. I've been all over the support site, the users manual, etc. It's like doing my tax return; I keep flipping around.

PhillyPhan,
THANK YOU!! You are amazing. Everything was checked as you noted, but when I clicked "sync" the missing songs were copied on to my iPod. I can't thank you enough.
Since you're so good, let me ask you this: I have two "purchased" playlists. Only one shows on my music library on the computer, showing 204 songs. However, there are two created on my iPod. One contains 226 songs, and the other 204 songs. How can this be? Once I tried to take off one of them, and I knocked out everything, so I'm afraid to try again.
Again, thanks.

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