Sometimes it shows up, sometimes it doesn't.

I'm using a 2nd gen nano purchased Dec '06 with a MacBook purchased in Feb '08. When I connect my iPod to my computer, it sometimes doesn't do anything, but sometimes it doesn't. The iPod won't display "Do not disconnect" and the computer, including iTunes, won't connect it to my computer, so I can't sync my music or scrobble my plays. Usually, if I come back in a few hours, there's a 1/3 chance that it will work. I can't find anything in preferences that would cause this issue. Any help is welcome. Thanks.

A good test (on a Mac) to see if there are any corrupted preference (or other iTunes-related) files is to create a new admin user account.
http://docs.info.apple.com/article.html?path=Mac/10.5/en/8235.html
Then, log out and log in to the new account (do not use Fast User Switching). In the new account, try connecting the iPod and running iTunes. iTunes will start with a fresh empty library, and this user will be using new user preference files.
If your iPod starts behaving normally, then you have narrowed it down to something in your normal user account that is interfering with the iPod connecting properly. It could be some preference file, or the iTunes library file, or perhaps some background process that you have running in the old account. But at least you know that the iPod is probably OK.
If the same problems recur in the new account, then there is probably some hard to diagnose hardware issue with the iPod.

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