If you have a bunch of DRM music through iTunes and want to stay legal, get iTunes Match for the year. It's $25, but it should allow you to then download all of that music DRM free. Just a suggestion since people have been mentioning all this drm stuff.
As fat as contacts, just sync them with google. It's pretty easy to do. Tutorials all over the web for it. I recommend google contacts whether you use an iPhone or not. Easiest way to get contacts onto every other ecosystem imaginable. Only google makes it that easy. Everyone else wants to keep it to their own.