IPod wont be recognized on windows

I am helping a Friend out that doesn't own a computer and trying to add music to his ipod classic. I had to buy a new adapter for it to hook up to the computer b/c he only had charger hook-ups, the adapter I got is a GigaWare but doesn't seem to be responding. I downloaded iTunes and read all the manuals for both iPod and iTunes and it says I need to look for an Icon to respond to iTunes so I can be able to upload music to the iPod but it doesn't want to be seen. What am I doing wrong?

Neither of 2 iPod Shuffles (both 1GB) will allow version 1.1.4 software to install - various errors occur: "can't unmount", another user is using it, an unexpected error occurred (-147 or somesuch), and of all these, the last one most frequent and varied in timing (i.e. doesn't return immediately but takes between 10 seconds and 2 minutes to return error).
So the nicely buillt-in iPod Updated does download the appropriate software (cool!) but seems to hang up with the Shuffle with various errors. Tried the 5 Rs per ipod on support.apple.com, and also made Shuffle was only connected iPod, as there are 2 firewire-based 30 and 60 GB iPods, 1 60 GB USB iPod, a mini, and 2 shuffles. Lots of wires but all connected to a powered hub or two, so easy to disconnect. Nice wanrings on low USB power levels but just in case…

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