Many thanks for all the responses about MP3 players and sites. I have a better picture of the various ways people manage this stuff. Not that I know exactly what I want to do yet. (I suspect the key here will be allowing myself to get a system that's "good enough", rather than trying for whatever is "optimal".)
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The thing that is stopping me from getting an MP3 player is lack of a radio on an iPOD. I figure part of the time I'll be using it on my NYC commute and with the way the world is, I'd like an FM (actually AM/FM due to the NYC all news stations, but no one would make that) for emergencies on it.
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- The "next best" Archon or whatever, because proprietary formats piss me off
- An iPod, because I don't HAVE to use their format and people seem pleased with the quality
I too am balking at the price. I may not do this until spring when my latest house improvements are paid off.