Nano III Syn Issues

Hi, I had my new Nano working great and had my music on it no problem.
Then I was offered to upgrade to software version 1.0.2 or something to that extent, I also had to upgrade to Itunes 7.4 before it would recognise my nano to begin with.
Anyway, the problem is that itunes created a playlist called 'Nena's Playlist' because it said my ipod was full, but I didn't want this so I deleted it.
Then it appears that all my songs have been wiped from my nano.
I repeatedly connect the ipod to my laptop and it syncs automatically but says that it can not update as the playlists no longer exist and then seems to disconnect my ipod automatically (on itunes I can see my original playlists do exist and contain songs) so I press ok and go to the 'music' tab on itunes and select the box that updates all playlists and all music, then I press 'apply' but it doesn't work, it freezes for a few moments then says something about a mass storage device error.
I've tried restring my ipod but it won't even do that - it seems to take ages and so in the end I disconnect it using the disconnect device button in my toolbar.
Does it sound like I need to do one of the 5Rs?
Cheers

Hi I literally tried everything.
I'd probably home in on resetting the i-pod (toggle hold on and off then when hold is off press and hold the menu and select buttons at the same time until the apple sign comes on
Select manual syncing when you are prompted too
Restart your computer and connect it - see what happens- let me know

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