IPod skipping iTMS songs - but only one account

Hi,
I'm not sure what my iPod is exactly. It's a 40GB mono screen iPod, about five years old. I thought that made it a 'classic' but perhaps not... anyway.
Since I updated iTunes last, the update deauthorised my accounts on my MacBook. One of these was my current account and I've got that up and running again fine. The second one was an old account from when I was on AOL which the nice Apple people kindly helped me convert into an Apple ID account and that, too, is now running again on my MacBook.
The weird thing is that that account won't play on my iPod. It just skips through all those songs.
It will however play them if I connect my iPod to my MacBook and play through the MacBook speakers. I've tried authorising it but it says my accounts are already authorised and anyway, I don't think that's quite how you do it on an iPod.
I'm sure it's something fairly simple but it's getting frustrating now.
I have tried doing a hard reset on the iPod, holding down Menu and the centre button but it still skips through songs on this one account.
Your help would be greatly appreciated.
Thanks
Charley x

Roaming: Heck! I think you are right. I'm not at home right now to check so I think I can check on that only through itunes. But, as I now recall, this happened to me before. These are all Christmas songs and I set them to skip after Christmas so "by artist" they are not included. The 158 are tracks added since last year and I forgot to set. Ugh!
Thanks for the tip and I'll update tonight once I confirm.

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