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Pocket Tunes has a feature that will allow you to sync with Windows Media Player. Realplayer has been designed for older pdas, and won't work. After you sync the songs on Pocket Tunes, they will show up in realplayer.
There is probably a compatibility issue between the TX, Pocket Copy, and Iphone. TX is pretty picky about what can be used to transfter information. They only recommend Outlook and the one that is included on the TX CD.
TX and IPhones are different systems as well. You could try to get the files exported from the TX into a CSV and see if you can import the files into Iphone that way, if it will import them.