Are you able to use iTunes match with your version of iTunes? If so, the one time yearly fee makes it simple as you have all your music on your phone all the time to stream, or direct download from the phone. I like it for the simplicity and how it unifies my media.
“If you are neutral in situations of injustice, you have chosen the side of the oppressor. If an elephant has its foot on the tail of a mouse and you say that you are neutral, the mouse will not appreciate your neutrality.” Bishop Desmond Tutu