Can't Import Some Songs or More than One - HELP

I can't get an answer to this question: why when trying to import multiple songs will the import fail. I have to go back and do 1 or 2 at a time -- huge PITA. Also, Musicmatch would allow you to "scan" a folder and it would faithfully scoop up every song you'd downloaded since the last time it ran and import it. Can itunes perform this basic function?
Any help greatly appreciated. I love my ipod, but itunes seems like it goes out of it's way to make this difficult (gee, i wonder why)!
30 gig video   Windows XP   ThinkPad T60

I can't answer the problem about the import failing, but you can tell iTunes to scan a folder for new music.
'File' -> 'Add folder to Library...'
By default, it copies the music files in the folder you selected to your iTunes folder, so you end up with 2 copies of the files. To prevent that and just have it list the files in iTunes, but not move or copy the files, you have to change some setting in Preferences.

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