Why Can't I Remove iTunes Purchases from my Device?

Now I know this didn't used to be an issue on my old iPhone 3GS, but am just not sure if it's to do with iTunes or the iOS.
Basically, on my phone, I have two playlists that I sync - one is all my music videos, the other is songs that I want to listen to at this moment in time and this **** changes regularly. Now the problem I have is that I recently downloaded some music and video content from iTunes using my iPhone, and after clearing the 'purchased' playlist from my phone and syncing to the pc, I still have the songs I purchased. I initially added the new music videos to my video playlist but quickly realised I had duplicates so have had to delete any of the new music videos from the respective playlist. I have purchased both music and videos before and not had this problem, or am I missing something?
Thanks
Martin

This happens to me too. I sometimes get duplicate purchased songs, the thing that I do is delete one of the duplicate songs. If you accidently delete the purchased content (videos, songs, etc.), your purchased content will be still saved in iCloud. If you buy purchased content on either the iPhone or on iTunes, it will sometimes produce duplicates. I am not sure why, but all you can do is delete one. This should work.
*If you are having issues completely removing purchased content from iTunes, you would have to highlight the song that you want to delete and hit the delete key. When you hit the delete key for purchased content, a box should appear asking if you want to keep the song or delete to the recycle bin. If you want to delete it from the iTunes library completely (I believe from both your iPhone and iTunes library), click on the delete to the recycle bin. When you go into the recycle bin, you will see your purchased content in the recycle bin. On the other hand, if you just want to delete the purchased content from Just the iTunes library and not the song altogether, you would want to hit keep the file. Which ever option you choose, the purchased content will still remain in iCloud, so if you accidentally hit the wrong button the purchased content is still located in your iCloud.

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