I don't know if I have anything new to add but I'll do my best (my personal tastes lean on long-format, less radio-friendly but definitely consumable music):

Burlington VT's Nest Materials (available at that hipster place in SF or by calling Radio Bean in Burlington VT or drop me a line and I'll hook you up). _not_ a hippie jam band.

Thinking Fellers Union Local 242. Get the one with the painted lightbulbs.

Yo La Tengo. You should already know that though.

Postal Service. Very very nice indie.

Pedro the Lion. ditto Postal Service.

Elvis Costello old singles, or latest stuff, ... sans 80sSure it's old. But his old stuff is good and his new stuff is good. His 80s and 90s weren't so good so maybe you missed it.

James Kochalka Superstar Another Burlington VT gig. You can get it from icebox records along with my (cough cough) band Charles, Dead or Alive. James Kochalka rules. His comics rule too. Get the one with Monkey vs Robot or with Hockey Monkey... or just do Get Whitey. You won't be disappointed. Humorous much fun.

Anything on K Records If you like indie rock music you might as well close your eyes point at their catalog and just purchase.

William Parker, Hamid Drake In the jazz section, find anything with either of these two on it. If you like it, subscribe to Signal to Noise magazine to get more like it.

Anything on Thirsty Ear Records Like K records but for jazz. I don't mean no sissy Marsalis jazz either.

But more than this....

Re-engage with radio, Rand.

I know this iPod control is big and cool and all... but we're talking about the difference between surf and search. Remember back in the day just going from one cool site to another by following links? Find some radio that helps you do the same to your ears. Search is great when you want to, but if you've been relying only on search, you miss some fun random gems and start to be your own echo chamber.

I recommend college radio for starters... if Clear Channel owns it then you can count on Blando content. WRUV (in Burlington VT) streams and it's total freeform. DJs do what they want. If you don't like it, check back in an hour, there's good DJs for nearly every genre. There's a place up in Washington with that sort of ethos too. You need new filters.

You've been wandering about, gazing at your musical navel for about 10 years now. All your friends who used to recommend music to you either failed you, or you failed to listen. You need to re-engage. Finding a good radio DJ is the start (as in, a station that lets DJs do what they want, and you actively tune in to a DJ who tends to play music you enjoy). It's hard work but worth it.

Also... have you rated the songs in your collection? Get on that stick man. Just set up a playlist that lets you rate unrated songs and go to it. 10 mins a day or whatever.

Keep it moving.