Failing transfers from iMac to iPod

I've won a free 30GB Video iPod and last night I set aout transferring my iTues Library to the new iPod. I had no idea how long such a step would take so i decided to do it overnight.
Just before going to bed I noted that it was transferring a Queen track. 12 hours later it was still tansferring the same track - it had obviously stuck.
Ejecting the iPod didn't, so the only way I could stop the session was to unplug the USM lead - not recommended practice I guess.
I started again and it stuck at the same place so i deleted that track from iTunes and started yet again.
This time it stuck on another track so I had to repeat all the "pull out the USB lead, delete offending track and start again" routine.
This has now happend five times and I'm still nowhere near copying the whole iTunes library - and the offending tracks play fine on the iMac.
So:
1 Why is it happening?
2 How can I stop it happening again when the "offending" tracks are put back into my iTunes?
3 How can I ever "automatically" synchronise if everytime I plug in the iPod it is going to stick?
I am an iPod rookie (and, for that matter an iTues very basic user) so any advice would me very much appreciated.
Cheers.

Thanks, Jeff. I've followed your tip and some loaded correctly after I'd reimported them from the original CDS and a couple didn't. Those latter have now been binned permanently.
But I have another problem: I am now importing my iPhotos onto the iPod and it has again "stuck". The problem is that, unlike iTunes imports, iPhoto seems to give no indication as to which specific snap is causing the problem. How can I identify and remove the offending picture?
If I just pull the USB plug on the iPod (the only way I've found of freeing a stuck transfer session), will all those prior to the sticker remain on the iPod so that I can just count to the offender, or will it lose some of them and leave me none the wiser?
Cheers.

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