I looked at your setup and it looks perfect. The iPod does not have to be plugged in to see all the options on the iPod (if I understand your first question correctly). You should see the whole menu the moment the iPod is switched on.
Itunes (or any music for that matter and the way way you get it onto the iPod) doesn't matter.
Try the following: Select the standard iPod mode (as the gentlemen and ladies at Apple wanted you to when you purchased the iPod), then do a reset of the iPod by pressing the menu and select buttons simultaniously for +- 5 seconds.
I have no further ideas for you - sorry mate (apart from restoring the iPod and starting again from scratch - which I know you did a gazillion times already)
Wow you have been hard at work here, but Sega Supperstar Tennis is not on the list, got to stick to the list. Try finding a game you own thats on the list. Then back it up. Test and post results. I havent tried using others backups. So i am in no position to help there. But i can make my own backups and play them.
Ipod 5gvideo + 320gb slim + 4gb usb memory stick + Ps3news = total happiness
Thanks to all who have helped everyone to achieve total happiness.
I tried to run backups with another bluray in drive, but it doesnt work. It seems that my ipod are not using the payload correctly.