Merlin sez, "Glenn McDonald has concocted a wonderfully byzantine bit of iTunes scripting that rates his music tracks automatically based on a number of factors. Great stuff. Perhaps most interestingly, though, he uses some of the resulting data from his listening habits to determine any outstanding 'payments' that he owes to the artist, dutifully paid via an automated perl script."
For artists who accept electronic payment via Paypal or credit cards, the database records the relevant payment info. A separate nightly perl script issues electronic payments (via CapitolOne's excellent web-services "micropayment" (sic) interface) where possible (batched until the amount exceeds $1.75), and for artists without electronic payment info, totals the corresponding amounts and transfers the overall total to the money-market escrow account I have for this purpose. The escrow account isn't automated yet, but I usually kludge around this, when I get new payment info for an artist, by simply moving the money back out of escrow, resetting the amount paid/escrowed to $0, and rerunning the original script. At the end of each month I mail physical checks to artists for whom I have physical addresses but not electronic, and rebalance the escrow account accordingly. I don't currently have a way to split this compensation across the performer and the publisher for material where the two are different. The best I can do is include track info with all my payments and rely on the artist in turn to pay for material they acquired from elsewhere.
I did an interview last month with James Schellenberg from Strange Horizons, on the kind of music I listen to while writing, as part of a piece on SF writers' listening habits. I hand-rate all my music and use iTunes's last-played feature to put together a rolling playlist of high-ranked music I haven't heard in 30 days or more, so I get to hear all my fave music (at least) once a month.
(Thanks, Merlin!)
Update: Turns out that this was largely a prank/hoax/speculation; from the comments on the 43 Folders blog post:
As various Davids guessed or noted, the intro and #1 through #4 are all exactly true, but starting with #5 the post migrates from what I actually do to speculation about what I *might* be doing if I had unlimited time and no other projects. The stuff about fingerprinting and admitting that (only) the last bit is geeky are cues, but most of the rest of it is plausible even where it isn't true.
In practice, for example, I actually don't use ratings myself at all. But several people have emailed me about that section after you posted this link, so now I'm thinking maybe I'll actually implement it. It's a good idea for exactly the reason you said: the software ought to respond to the implicit semantics of my regular interaction with it, rather than me having to make an endless series of explicit decisions about things. I probably won't build exactly what I described, which had some impratical fantasy wrinkles, but I've got the scaffolding for something on the same basic principles, which might be useful and/or interesting.
The compensation/micropayment thing, on the other hand, was an attempt to describe the absurd complexity an individual person would have to take on to administer such a system themselves. I wouldn't try to build this in reality, although interestingly, the new SQL Lite hooks in Tiger may make some of the database integration I described a lot more tenable than it is right now. My own artist-compensation system is much simpler: I still buy CDs. But this whole industry is on the verge of collapse and reinvention, and the new forms of it may look a lot more like my imaginary DIY version.