Ipod Shuffle - 2 Gen, 1 GB - not sync all songs and blank autoplay menu

Hi,
I have two issues with my ipod shuffle, 2 Gen, 1 GB.
When I attach it to my computer a blank autoplay menu pops up. Nothing can be selected and I just click cancel and it goes away but it comes up every time I connect. I've tried going into the properties of it in my computer and setting the default action to do nothing but it still comes up. I've also disabled disk use within the settings of it in iTunes but it still happens.
Second when I try to autofill from a playlist, it shows all the songs ready to be synced but after doing about 11, it stops and says it's completed when it clearly hasn't. If I press sync again it does a few more then same result. It just won't fill the ipod up. I've double checked there's room on there and I have set zero space for disk use so the entire 1 GB is used for music but it still won't do a complete fill in one go.
Anyone got any ideas? Using latest version of ipod software 1.0.4 and latest version of iTunes 10.1.0.54

My iPod Shuffle 2nd Gen (latest firmware + iTunes) is
almost only playing purchased .m4p songs. Only very
few (1-2 out of 200) of .m4a are playing on the
shuffle.
The songs are getting transfered properly and when
the shuffle is connected I can play the
songs/.m4a-files stored on the shuffle through Real
Player (The folder structure is accessible through
the FileExplorer while the upload process is
running).
If I only upload not playable .m4a songs the shuffle
blinks "no music uploaded".
Looks like a firmware problem of the Shuffle since I
can't see any pattern which .m4a songs are played and
which not.
Can anyone share this experience? Any solution?
WHAT does iTunes' Get Info "Summary" say about the songs that don't play?

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