Thanks for your responses, I’ll have a play around with a few things and see where that get’s me. I did try a free app on the iPad, a file browser, but when I try to connect to the PC via bluetooth it won’t connect, though the PC connects to the iPad without a problem and seems to play sound from the iPad through my soundcard, which is odd. I haven’t yet bought the track from iTunes I was just trying to send some photo’s, though I should be able to do this over wireless too.
trjp is right I should just rip the track of Youtube, it’s probably on there. Though I’ll still buy it on iTunes - I’m not a thief!