I hate to say it, but I was totally sold on the idea of iTunes Match, and now am completely turned off. I spent 3 hours on the phone yesterday with tech support trying to figure this issue out. I have about 30 gig of music on my Mac and a 16 gig iPhone. I want to sych about 5 gig of music through the cable using the playlist I have set up on my computer and manage there, I slide songs in and out of it depending on what I want for the day. This has worked fine for me, the benefit of iTunes match to me was that if I was out on the road and wanted a certain song, then I could download it on the go. To my surprise after I turned on iTunes Match, the ability to synch a playlist is gone. I played around with it and couldn't figure it out. I stopped at the Apple Store and they told me I should be able to and that something must be out of whack. Last night I spent three hours on the phone with tech support and the first two people said the same thing and kept trying to walk me through the process to synch a playlist yet I kept telling them the option is not there. Finally I got an "iTunes Match" expert on the phone who in a very straightforward answer told me that the way the system in working is exactly as intended. I said "hold on, so any music I hove that doesn't match to the iCloud will be pulled off my phone? Like the CD my sister made with her kids singing Christmas songs?" He just said "That's right". I'm still shocked this is how they intend to have the software work. I tried late last night to turn off iTunes match, make a playlist and synch it to my phone, then turn back on iTunes Match. My playlist included every AC/DC album, every Beatles album, and my sister's CD. When I turned back on iTunes Match, now I have all the AC/DC song files on my phone and all the Beatles albums except two of the disks (they are labeled as "Excluded" in iTunes now, yet I bought the CD and burned it myself, this is not a hokey stolen off the internet file) and get this, my sister's CD is there. It clearly seems to me that Apple has not thought this one through and they have tech advisers who don't even understand the product. This seems so simple to me, let me load whatever music I want onto my phone during the cable connected synch and then let me pull additional files as I want while on the road. Have you heard about the guy who has had his whole library load from the cloud through his cellular service, he is goona love his bill when he gets it.
