Hi MxA!
First, when trying to turn off your iPod, be sure that your hold switch is OFF (grey-colored), instead of ON (orange-colored).
What do you all mean cycling the hold switch? I'm kind of confused regarding that. Does this hold switch technique have to do with the sleep option?
Switching the "hold" switch back and forth, on-then-off, on/off a few times can work for some people if they're having problems turning off the iPod.
After "toggling the hold switch", and it is sometimes called, see if your iPod can appropriately turn off.
I haven't followed or kept track what you've said in your posts here, so let me start on a couple of basic things to try if you're having turning-off issues with your iPod.
Have you tried resetting your iPod?: hold the "Menu" and Select (center) buttons together for 7 seconds, then the Apple logo will appear on your iPod's screen.
Attempt
resetting your iPod (this will not delete any music off of it) several times.
If this doesn't help, then try a restore on your iPod. For more details, read here ->
Restoring your iPod
Also, connecting your iPod to your computer, ejecting it, disconnecting, and repeating that cycle several times can sometimes refresh your iPod and possibly solve your issues as well.
-Kylene
If any post helps or solves your issue, please mark it that way accordingly. Thank you for helping the boards!