No resume, hibernating or deep sleep?

My 5th gen Ipod (30Gb, video) goes into, from what I can tell, into something deeper than hibernation. It happens after about 12 hours after I turn it off using the Play button and holding it for a few seconds.
When I turn it on again I have to press the menu button. And then it boots to the main menu, and I have to select the playlist all over again, playing from the top.
Quite annoying when I want to listen to a certain album, because I get to hear the first tracks all over again when I was hoping to liste to the middle part of the album.
An by some means the randomness is weird. My 300 song playlist acts weird in conjunction with the above issue, it randomizes what feels like the 50 first tracks. So the next time I use the iPod, I get the same 50 or so songs all over again. It used to be a 500 song playlist but I have grown borde of what used to be the 200 first ones...
I've tried most things including resetting it to factory default but I might have done some setting I forgot about or overlooked some other setting.
Please help!

Thanks!
Sort of. I turn it off by holding down Play/pause button for a few seconds.
So it enters Rest-mode. And if I leave it that way it goes into Deep Rest-mode?
The issue for me, is that it doesn't resume play on the playlist I listened before I turned it off. Is that normal?
I have to power it up using the Menu button which sends me to the main menu and I have to select the playlist again upon the iPod starts all over again on that list, which I don't want it to.

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