ITunes won't allow disk use of Reset iPod

I'm using a 40Gb click-wheel iPod for music and as a hard disk for file transfer, which has behaved fine up until now.
Just recently it took to skipping through Audio Books so I plugged it into my computer, up comes iTunes (latest version) and I hit Reset - iPod is reset, all the music loaded back onto it, but now when you set iPod options within iTunes they're not remembered.
I want to turn off auto-boot of iTunes with iPod detection, and turn on disk use. When I make these changes, iTunes takes ages to close, and when its re-opened the changes are not made.
Help would be greatly appreciated
jON

The tracks are not eligible for icloud; they are personally recorded lectures.  If I try to manually add them to a playlist I get the warning about the playlist being removed from icloud and only available on my computer.  Is this what I need to do in order to have both my recorded lectures and the rest of my library in itunes match?
unsure of bit rate...but tracks are not in the cloud.
Thanks Jim
Dave

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