Can't manually update songs through iTunes

I have had my iPod mini and iTunes set to let me manually transfer songs for almost a year now and updated to iTunes 5.0 a few weeks ago. I didn't try to update my iPod until tonight, and now iTunes is not letting me click and drag my songs to my iPod.
I have tried using Add to Library and Import, none of that works. I also went to all the help windows and webpages I could find, but all those did was brag about how you can automatically sync. (I don't want to start syncing automatically because I have 500 songs on my Mini and only about 30 on my computer; I'd lose everything.) I've also tried restarting my computer and plugging the pod directly into the computer.
Is there something really simple that I just overlooked?

Well I'm not updating my iTunes any more, that's for sure.
I finally figured it out: the two songs I was trying to put on the iPod were iTunes Free Downloads. They must have a hidden limit on the number of free downloads that you can put on your iPod. I'm able to update with songs off of CDs or songs I've bought, but not the free ones. I can still get them onto iTunes, put not onto the iPod.
Personally, I think that's a rip off. A "free" download ought to be entirely free. Why download it if you can't put it on your Pod and take it with you?

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