I signed up for iTunes match a couple of months ago when I got an Apple TV because I wanted to try it out. As someone with 75 GB of music and a 32GB iPod (and now a new 32GB iPhone 5!) it sounded like something that I can really take advantage of. However, I've had some major problems with it that have prevented me from using it much. In fact, I haven't really listened to music much at all since getting iTunes Match because I feel like it's too much of a hassle now. Here are some of my main concerns. 1) Previously I could create a playlist and sync my iPod to that playlist. I would put all the music I wanted into that playlist and use it to manage what was on my iPod and how much space music was using. Now I want to sync that same selection of music to my new iPhone, but it seems that the only way I can do that with iTunes Match is to download each album individually from the iPhone. The only way that I can think of to work around this is to turn off iTunes Match each time I want to re-sync my music. 2) I also created two automated playlists that I've used for years to make loading new music onto my iPod a simple process. I have one playlist that automatically includes any new music that I've added to iTunes over the last 30 days, and another playlist that has any music that I've listened to over the last 30 days. When I download a new album, it gets added to the iPod the next time I sync, and if I listen to it periodically it stays on the iPod. If I forget about it and don't listen to it it's gone after a month and no longer takes up space. Now with iTunes Match, when I import a new album, I have to first sync my iTunes Match library and then find that album and download it again to the iPod. Is there a better way to add new music to my iPod/iPhone each time?