I have seen a similar problem to this. Traced it to Windoze assigning the Ipod the Drive letter A ...and thinks it is a floppy!
Fix was to stick a USB memory key in FIRST ...that will take the A drive assignment then stick the Ipod in. It should then get E/F/G .. whatever.
You can then go to Disk Management and change the drive letter to a letter further down the alphabet. Once you have done that it "should" then recognise the Ipod each time and you won't need to use the USB key trick each time.