Topic: LaLa.com Widget
More than anything else, I would love to see lala.com on the Chumby -- and I think it would be as viable to do as pandora/shoutcast/iheartradio.
lala.com allows you to upload your drm-free mp3's to them, you can then listen to your music library free of charge from any computer with the Internet and a webbrowser. (My hope here is to add "and chumby" to that list). Totally free. And they use no advertising on the website, so while with some companies they might drag their feet going Chumby as they'd lose ad revenue, that's not an issue here.
It also acts as a music store, allowing you to purchase web-streaming-only songs for 10 cents or downloadable drm-free mp3's for 89 cents. Perhaps, like with Pandora, we could link our chumby to our lala.com account, so we could purchase the tracks fright from the chumby. It would effectively be bringing both a music store AND the ability to stream your library to your chumby without having to muck around with third party applications. (It would also mean I could bring my music with me, in form of my chumby, any time I travel and have Internet).
http://www.lala.com
(Or, if you want to earn me a handful of free songs you can use the referrel link below)
Full Disclosure: Shameless Referrel Link
Edit: Amending grammar fail