Well, I finally bit the bullet and paid for iTunes match. I had been using google music through the GMusic app on the appstore (very good by the way). Unfortunately, this doesn't play well with the Nike + GPS app. Said app grabs onto the music app and won't let go. I finally got sick of fumbling with this on runs, so I figured iTunes match uses the stock music app, so all should be well. Well, it is, in terms of Nike + GPS. It is not, in terms of syncing my music. I don't buy any music on iTunes, namely because it is often cheaper elsewhere. My problem is that about half my tracks were not matched, but rather uploaded (I have around 3000 tracks). Of the tracks that were uploaded, there are maybe 100 that are not on iTunes. Most everything i own SHOULD be getting matched and not uploaded. So what do I have to do in order for iTunes to recognize them? Everything is 192kbps+ MP3 format. I did do a bit of searching, but didn't find a real conclusive answer. The best I could find is someone recommending conversion if you had some really old low bitrate tracks, variable bitrate tracks, etc. Basically, none of the scenarios applied to me.