My Brother's iPod Nano Is Having All Sorts Of Problems. HELP!!

Hi. I'm new here and I recently handed down my 1st Generation iPod Nano to my brother and I bought a new one.
Now he is having issues with it that I never ran into when I owned it. He can't drag and drop the songs onto the iPod, it randomly disconnects when he has it plugged in, and then it randomly gets recognized by the computer again and starts auto-updating all the time.
It also says something about the proper software to update iTunes is missing, and that iTunes needs to be re-installed.
We've tried reinstalling, and we still run into the same problems as previously mentioned.
I'm wondering if it has something to do partially with the sync options and software versions, and also with my brother's PC being pretty broken down.
Help PLEASE.

On my computer it doesn't randomly disconnect like it does on his, but it still wouldn't let me drag and drop AAC files onto my iPod towards the end of me using it, and it used to let me easily drag and drop.

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