The entire 8-page article is worth the time to read. But this quote stood out and may describe one big weakness to the iPod/iTunes model:
“All this stuff (internet radio, subscription models, Pandora, Last.fm) is Apple’s blind spot,” says Fred Wilson, the New York venture capitalist and rabid music buff. “Right now, the download model is necessary because I want to take music in the car or to the gym. But once we have true mobile broadband, the streaming model is going to take off. Then there’s never really going to be a need to own files at all. It’ll all just be there in the cloud.” As for music discovery, Wilson says, “I’ve never found one single artist or song on iTunes … It’s an online version of Tower Records, only worse.”
I can’t wait for the day when I can share my playlist with anyone and my podcasts and music are sync’d to all my PCs, my car and my phone. In the meantime, I will buy CDs and rip them to MP3 where I can upload to my iPod.
Nordquist Blog 