I am at a point in my life where I can plan a year ahead to what my next music purchase will be.
My next music purchase will be something by Roy Buchanan. If I'm lucky, the multi-CD career-spanner. If I'm not, it'll be the Millenium Collection. Not to knock the MC; I have the ones for Cream, Clapton and Skynyrd, and with the exception of "Ballad of Curtis Lowe", I cannot think of a first-grab song from Cream, solo EC or Skynyrd that isn't on those. Good collections.
But as my music money is more and more spent on gas, new brakes for the wife's beater, a hot water heater, etc., the more conservative, in a bad way, my purchases are. Take Roy. Open Masters of the Telecaster you'll see sections on Danny Gatton, Clarence White, Cornell DuPree, James Burton, Steve Cropper, Muddy Waters, Albert Collins, Keith Richards, and Roy Buchanan. When Arlen Roth wrote the book on the Telecaster, he made sure that Roy Buchanan was in there. I've already received a guarantee that this guy is good. Does it mean I'll like it? No, but it's a good guess. It's a safe choice.
After that, I'll likely get GP/Grievous Angel from Gram Parsons. I've listened to it before. It's good stuff. It was directly influenced by people and songs I really like, and a direct influence on other people and songs I really like. So, very safe.
Everybody has their version of this. Reviews. Word of mouth. Radio. I once bought an album because it was on the Onion AV Club's best-of-the-year list and the influences seemed to line up correctly. It was Marah's Kids in Philly. And it never did much of anything for me.
Just to explain, but safe doesn't mean easy. For me, buying an electric Miles Davis album (1968-1975) is a safe choice, because I know the style and I know I like the style. Buying a Hannah Montana album is dangerous because if I like anything, I'll like one track at most and I'll never play it again, thus wasting my money.
What I download for free is a little more diverse. I can afford to be more open because I'm only putting my time into it, not my money. Most of my listening occurs when I'm doing something else, like programming or driving, so that's "free". But even then, when I look at my most recent downloads, I see safe decisions. I wanted Metal Fatigue by Allan Holdsworth as a teenager, but my local record store sabotaged me. And White Brothers live tracks and practice sessions are safe choices for a guy who bought Sweetheart to Farther Along simply because Clarence was on 'em.
Right now, I'm hearing good things about Nels Cline. This comes after finding less and less to listen to in the band he's been in for 3 years, Wilco. A.M. is still my fave-rave Wilco album. From The Woodshed is all about Nels, and I've heard good things about the Nels Cline Singers album. There's a specific name-check, comparing him to later Coltrane and mentioning that he played Interstellar Space that is really drawing me. (Live in Japan was also a recent download. It's ... a bit much for me so far. Not that I've stopped trying. I'm just giving it a few months.) So, with Nel, I'm worried.
Those who know, are there assurances? Is it safe to queue up Nels Cline? Is Instrumentals more Pangaea or Kids In Philly?