I can't sync a playlist on my imac, 2 years old, to my iPad 3years old

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i have managed to amend a playlist with two new tracks on the iMac and sync them to my iPod which is 4 years old.  But when I wanted to add another track the iMac wouldnt have it!
i Can't sync the playlist to the iPad, at all.
i Am completely brassed off, having spent hours on the www trying to find the answer.
someone please help, King Penguin are you still there?

Right, rented movies do not sync.  They must exist on only one device.
See "Can I play my rental on more than one device?" here:
http://support.apple.com/kb/HT1657

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