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Microsoft and iTunes

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I am not the smartest tech person so please bare with my elementary questions....that's why I'm here!

I am sick of iTunes, but I have downloaded a bunch of music from them and I now want to convert everything over so that I no longer have to use this frustrating program that doesnt seem to allow me to use other multimedia devices besides my iPhone to listen to music. Best way to do this and not lose any music I purchased?

Also, even if I do stick with iTunes/iPhone, when I create a playlist on iTunes and try to transfer it over to my iPhone4, some of the songs on the playlist do not transfer over and I am left with only a select few of the songs after I disconnect. Please help with these!!

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