Issues with getting songs to update to ipod

I have a collection of 6000+ songs, only 3500 will update from my library to my ipod. When I select the songs that will not update I get the message that they song is not authorized for my computer along with the pop up box to authorize it. Once I have authorized it to my computer it will give me the not authorized message again and just keeps me in that loop. I can not get the music to copy to my ipod or play on my computer.
I would really appreciate any help, I cant get this to work.

aha, but there IS a way around this; forgot exactly how I did it (4 yrs ago), but it had something to do with copying the mp4 over a network to an old OS 9 Mac from a windows XP machine where it was purchased.
I am positive I did it with a file purchased on iTunes Store and it wound up being mp3 when I was finished; radio station still has it last I checked.
somehow copying between different OS's did it. At the time (like now), I had to have mp3s for our radio station I used to work at. We paid dearly for music licenses every year. however, some songs were impossible to find in their original release style.
experiment with that if you are good with computers and that is possible, otherwise you're stuck having to go to another music download site as previous reply suggested.

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