Loading dupliacate songs via playlists....

Maybe this is not the right way to do this, but.....
I have created a playlist in iTunes to contain songs I want copying to my Shuffle (makes it easier to manage them - I just drag the playlist to the shuffle and it keeps synchronised)
Anyway, the songs on the Shuffle are played "shuffled" but I'd like some songs to appear more often - so I copy them into the playlist multiple times and click "add" when iTunes tells me I am adding duplicates
Now, I have a playlist with duplicates - so far so good
Snag is, when the playlist is sync'd to the Shuffle - the duplictae entries disappear and every song is there only once.
I can MANUALLY add duplicates to the Shuffle, but surely duplicates in a playlist should be synchronised "as is" anyway
Suggestions/Thoughts welcome
Thanks
Phil G

OK, this just got a bit odder
I noticed that the list of songs on the Shuffle was missing more than just the duplicates and no matter how hard I press "sync", although it looks like it's syncing, the naylist stays different
BUT
If I manually delete all from the Shuffle and THEN sync - ALL of the tracks get copied - including my mysterious duplicates
This can't be right
I have 50 songs in a playlist - sync'd to the Shuffle so there are 50 songs there too
Add one song to the Playlist - now 51 songs there. Sync and there are still ONLY 50 on the Shuffle......
What I am I not understanding about the iPod Shuffle synchronisation process??
Thanks

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