After being really happy with the Nokia Multimedia Transfer app for OS X to get music onto my phone, and photos off it onto iPhoto, I started looking to solve the "where to get new music" problem.
Around the same time, I was playing with the Nokia Podcasting app. Put simply, it is a podcast browser / downloader, which you can set to automatically connect to a network connection and download new podcast updates at a specified time. I set my phone to charge overnight, and set it up so that it would auto connect to my home wi-fi network.
Then I found Hypemachine. Yeah, yeah, I'm not really a cool trendy new music guy, and I *had* heard about it before, I just never really used it: it's a giant blog aggregator that tracks mentions of music and links to MP3s. It also exposes all this music blog aggregation as a podcast, with enclosures to the MP3 links. Not a traditional podcast at all -- it's whatever the Hypemachine has auto aggregated during that time period.
So, every morning, my phone is loaded with brand new music. It's eclectic to say the least -- last Friday featured lots of 4th of July-themed songs. The first time I set it up, I got some nice Catholic-rock-band tunes. Last night, I copied that music back to my computer after about 2 weeks of doing this. 63 songs survived my listening over that period, and I cut that down to about 40 that I would keep / give at least 3 stars to.
I'm listening to a lot more music on the go with this setup, and am being exposed to lots of "new stuff". So far, I bought the new Cold Play "Viva la Vida" album (definitely not a "long tail" band), as well as Ra Ra Riot both as iTunes Plus downloads. But the majority of the bands seem to be ones that I need to point you to their MySpace page to listen to their songs -- see Hooded Fang for one example.
It's been a fun experience so far, and I always look forward to what the next night of downloading will bring me. This whole listening to music on the go thing might really take off one of these days :P
Where do you find new music? Where do you listen to it? Where do you buy it?