Everything in our house is apple. iTunes on the Mac, IPad, IPhones, and IPods. We are in the process of purchasing an Apple TV and an Apple Time Capsule. I keep my ITunes extremely well organized with albums cover art and information being up to date. It translates extremely well across the different devices that way.
This. I'm way too lazy and don't listen to music on my computer often enough to really bother looking into anything else. 99% of my music listening is either on my phone or ipod, while driving or at the gym.