Recently, Google announced Google Music Beta. My understanding is that with Google Music Beta you can upload your entire music collection to the web and listen to your collection anywhere with an Internet connect. Currently, it looks like there is only an Android app for phones and tablets that will allow you to play your music when you are connected to the web and downloads your recently played music for times when you aren't online. I'm assuming it is just a matter of time before there will be an iPhone app.
Currently, Music Beta is by invitation only. I requested mine today.
As an educator, you probably use multiple computers, so it might be nice to have access to your music and podcasts from any computer you use.