Can't update software, iTunes songs won't transfer

I have an older docked iPod (2nd gen, I think). It is running iPod software 2.2. I updated iTunes to the latest version and now my recently downloaded iTunes songs won't transfer to the iPod. I get an error message saying my iPod software is outdated. But I can't get the latest iPod update software to load. I've downloaded it twice now. When I go through the installation program, it shows me the possible destination volumes for the software -- either my iPod or my hard drive. The iPod has a red X next to it, with an error message saying the software can't be installed on a volume that doesn't have OS X 2.8 or higher on it (my Mac is running OS X 10.3.9). If I try to install the iPod software on the hard drive, everything is grayed out and says disabled. I don't know what to do next. How do I update the software so I can transfer my new playlists? Should I downgrade iTunes back to its previous version (if this is even possible?)? Help! Thanks!!

I have an older docked iPod (2nd gen, I think). It is running iPod software 2.2. I updated iTunes to the latest version and now my recently downloaded iTunes songs won't transfer to the iPod. I get an error message saying my iPod software is outdated. But I can't get the latest iPod update software to load. I've downloaded it twice now. When I go through the installation program, it shows me the possible destination volumes for the software -- either my iPod or my hard drive. The iPod has a red X next to it, with an error message saying the software can't be installed on a volume that doesn't have OS X 2.8 or higher on it (my Mac is running OS X 10.3.9). If I try to install the iPod software on the hard drive, everything is grayed out and says disabled. I don't know what to do next. How do I update the software so I can transfer my new playlists? Should I downgrade iTunes back to its previous version (if this is even possible?)? Help! Thanks!!

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