Where  is my old music?

I have an imac and two ipods. I updated music in the playlists and connected an ipod. I received an error message with instructions about updating software, which I followed. Following reboot, I connected an ipod. My ipod only has recently purchased music, nothing old. I now have three songs. All the old stuff is gone. I tried to change the settings for what to upload, but it made no difference. I am going back to a PC. If I have to deal with this nonsense I might as well pay less for it. Any ideas as to how to get my music back on the ipod? I am extremely frustrated with what should be a simple and 'fun' task.

Welcome to Discussions, Michelle.
I am going back to a PC. If I have to deal with this nonsense I might as well pay less for it.
Please don't be so hasty. Trust me: in the long run, you'll be dealing with much less "nonsense" on Macs. And there will always be plenty of people here willing to help with whatever small problems you come across.
I'm assuming that you still have all the music on your computer, playable in iTunes.
You said that you have two iPods, but never distinguish them — Did you connect the same one after the update? Have you tried the other iPod?
With one of the iPods plugged in, check its preferences and make sure automatic sync is selected. Then, control-click on the iPod in the iTunes source list and select update. What's happening now?
If it still doesn't work, you might want to try opening the iPod updater (located in Applications > Utilities) and Restoring the iPod (I'm assuming you don't have any files other than music on it).
Report back. Good luck.

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