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1) I haven't heard of most of them. You can't promote a nobody band if you can't even promote your website well. By "well", I don't mean "first page of listings on Google".
Yeah, this is a big complaint of mine. Most of these sites seem underfunded enough that they don't have the budget to get themselves out there. That's why I'm convinced that I'd need some financial backing to make this work. I'm sure I could get some friends together and develop a web site in may spare time if I really wanted to (though that would effectively kill my spare time devoted to the band- it's difficult to make multiple spare time project work), but "If you build it they will come" does NOT work in the real world.

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Scouring those websites is too much effort. I like music, but I don't like it so much that I'm going to spend hours of my day looking for new stuff . . . if getting new music is any more difficult than turning on a radio, or hitting go on a long streaming playlist, then I'm just going to listen to what I already have.
Another vote in favor of a passive experience, where you are streamed selections. Of course, if you truly don't want to put any time in then the best I can do is stream you "people who liked artist x liked these songs" or "these are the highest rated songs in genre y"- but that's still a lot easier than scouring a site looking for bands and never knowing what kind of quality you're going to get. But if you're willing to vote on a couple of songs or even list your favorite (or least favorite bands), the site can begin to custom select music to better hit your tastes.

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For an example of the latter, a few weeks ago, I was reading a +5 post from a guy on slashdot, discussing promoting something when you're not already famous. He had a link to "a major mp3 blog" (mp3 blogs? didn't even know they existed) where he had a sample track with more downloads than a track from bjork. That made me curious, so I followed his link just to see what the fuss was about. (Incidentally, I really dug it.) . . . We're so accustomed to having music pushed at us, that to have to go looking for new music will nearly forever remain the domain of the hardcore listener.
I think the key here is to be able to capture the hardcore listeners and give them easy ways to draw in the non-hardcore listeners. After all, word of mouth is the best promotion.

What I'm currently envisioning is a system in place so that fans could easily provide links to the artist's page on the site and then be rewarded if people click the links. So if I'm a huge fans of NewIndieBand, I can use my special link to their page and referr my friends. If I get a lot of friends to visit the band's site then I might win a prize- or maybe I'll just be listed as one of the "top fans" on the artist's page.

Of course, this kind of involvement is much deeper than most music fans are willing to go, but every band has a couple of fans that really want to help out in every way they can. So the idea is to give those fans the tools to really get out there and promote the band for you- after all, the best promotion is word of mouth. In fact, this concept is lifted from our own site where we have such a referral system in place. It works pretty well- not only do we have referral contests, we also have plenty of stuff to keep people engaged- we offer fans free downloads for registering with our site (which gives us a nice mailing list we can use for sending out email by zip code as we do shows), a band forum, a gallary for pics, and even a chat room. These are the kinds of features that devoted fans of a band would appreciate.

So the idea here is to give passive people playlists that match their tastes, and hardcore fans tools and motivation to interract with their favorite bands and promote them to the passive bunch.

See- our site does a good job of capturing fans once they get there- it's getting them to our site that's the problem. But if your had a bunch of artist sites, all with the same basic features (forums, pic gallaries, fan lists, referral contestes) then you'd have this common interface that makes it all comfortable. And fans of one band might look at what other fans of the same band might like. Each fan can have (if he or she likes) his or her own page with bio information and a listing of the bands of which he or she is a fan. The starts creating a network of the truly devoted and helps leverage relationships and "word of mouth" type referrals. This concept is borrowed heavily from myspace and works really well there.

The thing about myspace is that it doesn't work for the non-hardcore like you. There is no way to find music there unless you are truly willing to get invovled and start exploring these relationships between bands. I think it is key to make the experience as deep or shallow as the user wants it to be. If all you want to do is stream some music and hear some new tunes- it should be as easy as clicking a button. If you want to reall dig deep and interact with the band and other fans, those tools should be easily accessible.

. . . yes I've been thinking about this way too much. And my intent here was to really find out if I'm hitting the mark or not with my ideas. Of course, empeggers are only one type of listener out there, but the feedback I'm already getting from you guys is helping me flesh out (and possibly reject) some of these ideas. I appreciate it a lot!
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-Jeff
Rome did not create a great empire by having meetings; they did it by killing all those who opposed them.