Its fairly easy, once you ID3 tag all your mp3s correctly. If you are one that doesn't care of apple products much, the nomad is for you. My only real complaint is size. I've had to repace mine twice now (I got the bestbuy warranty, worth it imo) but that was only because the headphone jack was under sustained pressure from my aux input to my deck, anyway I fixed it now. Battery life on the newer ones seems much better, easily lasting two weeks of daily driving/listening while walking to class. I will note though, it likes the cold over the heat. I left it in my car in SC over the summer and it heated up so much it wouldn't turn on, didn't do any damage though. Overall, I highly recommend it.