IPod not synching as "there is not enough free space" (but there is)

I have a 64Gb iPod touch which I have been having problems with since I bought it.  The problem I am going to decribe has happened three times.
To the best of my memory, this is what has happened.
Starting with a newly purchased  iPod I synched it with my existing library.  This worked and I was able to play songs on the iPod with no problems.  The iPod still had around 8Gb left unused. A few days later I imported a few (maybe 3 or 4)  new CDs into my iTunes library and hit Sync.  The Sync process got as far as step 5 of 5 and hung, I left it for a good hour and it got no further.  I think I may have switched everything off and on again and then retried, this time I got a dialog box saying that the iPod cannot be synched because there is not enough free space to hold all the items in the iTunes library (additional 40Gb required).
Looking on the iPod I could see the full track listing for all my albums, but everything now had a red circle with a dot inside, and was un-playable.  It's as if the songs were all still on the iPod (taking up disk space) but the index had somehow lost track of them (or something).
The only thing I could think of was to reset and restore the device, I also deleted and re-created the iTues library and started again, re-importing everything. Again, this worked fine until I later on inported a new CD to the library and tried to re-sync, whereupon exactly the same thing happened.
I have not been able to find any support questions with quite the same problem I am having - has anyone encountered anything similar and have a solution?

It does have a red circle inside, but I am on Windows 7 and have not upgraded anything.
My problem looks similar to this one Re: iTunes library disappeared, re-added all my songs now iPod doesn't have enough free space to sync.
I can solve it by a compete restore and resync but when I try to add something and sync again I get the same problem and it seems like the only think to be done is to restore everything again, which clearly I can't do every time I add a new CD!

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