mmmmkay... Are you trying to take songs from like your Limewire folder? if so, go to file, add file to library, and choose whatever song you want. I just highlighted the whole thing and picked out the songs i didn't want. Then hit open and they are all there. A big problem, some of the song names are messed up so you have to rename them (ie. Audioslave-cochise, not Audioslave - Cochise) so you have to go through all the other songs and that takes so long.... sorry for the bad news, but good luck lol.
Ohh, to put the songs onto your Ipod (your playlist) just plug it in and let it update. It takes all your songs from your library and puts them onto your ipod. I don't use playlists... IMO it is much easier/better to just go by artist.