Unable to add tunes to library

I have tried to add a few songs to my library so I can put them on my iPod Nano. It doesn't want to add a few songs and I have no idea why. It'll add some tunes but when I went to add two tunes from one band and three tunes from another, it won't do it. Considering these are tunes I want on my iPod, this is kinda ticking me off as I've just spent an hour trying to get these tunes to be where I want them.
I had DL-ed these tunes off of Limewire (as most of my tunes are) and have no problem playing them on winamp (on both my work and home compy). Winamp is the default player on both machines.
What the heck is going on? Why won't it let me put these in my library so I can get them onto my iPod? Is there another way I can get them on my iPod? Assistance on this would be appreciated.

Your iPod is set to automatically sync all songs from your iTunes library only. If you just want to put certain files on there you have to enable manually syncing. Connect your iPod and click the iPod icon on the source list. At the bottom, under options, there is a check box that ask you if you want to manually sync iPod. Check that and click on apply. Now you can just drag your music and sync to your iPod.

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