Problem With Syncing

When I connect my iPod Touch to iTunes I can see that after the Touch has synced half the songs in my new play list are listed in light gray text and have a circle in front of them (this only occurs in my Touch not my actual iTunes).

I also can't play these songs when they are connected to iTunes but if I disconnect the Touch from my computer the play list on it is fine and the songs play.

Additionally iTunes will create a second copy of this play list in both my computer and my Touch after Touch has finished syncing (which is very frustrating).

I'm not sure if this is relevant but previously when I connected my Touch to my computer and went to Settings\Devices\Bluetooth & other devices\Other devices both the iPod Touch and the driver would be listed there, now only the driver is.

Any help would really be appreciated.