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In need of some techie guidance

Here's my problem:

I have the iPod Nano that holds 500 songs. But I've downloaded more than 500 songs to my iTunes account.

Here's what I want to do:

I want to download (or upload?) some of my songs from iTunes to my iPod. I do not want to delete any of my songs from my iTunes account since, duh, they're paid for.

Here's what I understand I CAN do, but don't know how:

Supposedly you can create playlists (which I have) and then choose which playlists to download (or upload) into your iPod. But I don't know how to do that. When I plug in my iPod and iTunes is open, it just automatically starts down(up)loading and then it gives me a warning or an error message that says there are too many songs to down/upload.

If you know how to do this, please leave me instructions in the comments. I'm so helpless. They'll need to be step-by-step instructions starting with how to set up my account or whatever. De. Tails, people. Thanks!