What's going on? conflicting information....

I have a first gen Nano, and the iPod software on it is v5.1, which iTunes tells me is up-to-date. In fact, the check for update button is greyed out, so that seems to confirm that.
I currently use iTunes 7.1.1.5 and keep getting prompts to upgrade to v6, which I really don't want to if I can avoid it. I know can't purchase some songs from iTunes now, as I require this later version.I always have problems when i upgrade versions - are there any known problems with this version on first gen nanos?
anyway, my main problem now is that the songs that I can still purchase with my 'old' version of iTunes can't be transferred to my iPod - I get a message that says 'some items of the itunes library were not copied to the ipod as the ipod software is too old. Go to the summary tab and update....etc etc'
so what do I do? One part tells me my ipod software is up-to-date and there is no update avail, the other tells me it's too old and to update? huh?
thanks in advance to anyone who can explain this to me.

Ok, so I tried again this morning and now the songs transfer without problem to the ipod - no error message at all. Hmmmm.
I'm now thinking about upgrading to the latest version of iTunes, but still a little wary as I've had problems with iTunes upgrades previously and having to restore my nano as a consequence.

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