Syncing with iTunes
One of Apple's stickiest technologies is iTunes, which is both a library for your entertainment and store from which to get more of it. Google's free Music Manager app for Windows and OS X syncs nonprotected music wirelessly to your Google Play account, but that requires streaming it to your Android device.
A better choice is the free DoubleTwist Player app, which syncs music, videos, and photos. Also, it can transfer these items from iOS device to Android. You need both the Android client and OS X or Windows client. Note that DoubleTwist is full of come-ons for in-app upgrades -- annoyingly so. The $5 AirSync add-on is worthwhile, as it allows Wi-Fi syncing between your computer and Android device.