Problems with iPod Nano 6th Gen Playback & Updating

Hi. I have had a look and can't find another post on this - apologies if I have missed it!
My problems start before I purchased my new Nano 16GB last week.
When the last update of iTunes came available, I was unable to install it. The task bar would get to about 50% (although it varied) and would then time out. When I had this problem I tried everything from every forum imaginable, from deleting all Temp files, disabling the firewall and all start up applications and clearing the registry – everything. Nothing worked. Eventually I decided that I should uninstall, then install the new version.
After a week of the same problems trying to install iTunes, I gave up and downloaded on another computer, and saved the .exe file to a USB stick. This worked until two days after I downloaded it, yet another update came out and I had to start all over again (I didn’t – I am running on 10.1.2.17 still).
I was concerned when I purchased my new Nano that I would have problems connecting it to iTunes as I was not running the new version – but it was okay. Unfortunately, the iPod requires update 1.1 and I am also having the same problem with this – I get time out error 3259 after sometime trying to download it. And yes, I have tried all the same tricks, but nothing seems to work.
I am running Vista on a Dell PC, and connect to the internet on a pre-pay internet USB dongle. I can download updates for other programmes, and other files successfully – it is only iTunes that I am having an issue with. ITunes is added to my list of accepted programmes on my firewall, but I disable that when I am downloading.
Meanwhile! My new iPod is fantastic. Unfortunately I am experiencing an odd problem with it, and cannot seem to find other people with the same issue. The memory is not overloaded (it has 1.10GB of free space on it). I have 1857 tracks on it, and 14 podcasts. I play the music files through the ‘Songs’ menu, on Shuffle mode. For some reason, after playing one or two tracks, it doesn’t seem to want to play the next one. The track will be displayed on the screen, but it does not play. When you look at the song progress bar, it shows that it is part way through the song, but it is not moving. I have tried pressing ‘Pause’ followed by ‘Play’ and nothing happens.
The only way to get it to start playing again is to skip to the next track, but even this has its issues. Sometimes, when you skip forward a track, it plays a completely different track to the one that is displayed. When you look at the progress bar for the song it is showing, it isn’t moving, but music is still coming out!
Does anyone have any idea what the issue is, and how I can get the machine to play continuously without having to handle it several times? Please?!

Hi dianak22!
I have an article here that can help you troubleshoot to resolve this issue:
iPod nano (6th generation): Hardware troubleshooting
http://support.apple.com/kb/TS3474
You can also walk through the steps of troubleshooting using the troubleshooting assistant, which can be found here:
Apple - Support - iPod nano (6th generation) - iTunes Troubleshooting Assistant
http://www.apple.com/support/ipodnano/6th_generation/assistant/itunes/
Thanks for using the Apple Support Communities!
Cheers,
Braden

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