"Come on. The buy-burn-rip option is offensively inelegant and wasteful. The DRM workaround I had in mind was JHymn, which is geeky enough that I wouldn't want to talk my Mum through it."
Unfortunately JHymn doesn't work so well just now. There is hope: haxx04rs have been able to intercept raw unencrypted AAC frames from ITunes 6 and 7, but this rudimentary work hasn't made it up into the handy Java UI that JHymn sports. As for the buy-rip-burn option, I agree that it's inelegant and time consuming, but I'd like to point out your tacit assumption that you'd be importing the music back in to the computer. Once you burn an audio CD with iTunes, the DRM is basically defeated, if you have any practical use for the item you've just created (gift, boombox, car changer, etc). If you want to go back into the computer you can either import is as Apple Lossless in the case of iTunes, or FLAC in the case of anything else, and though your file is larger than it was you essentially suffer no loss of quality for your trouble, and the DRM is still gone. This all begs the question though: Why in the hell would you ever buy music through the iTunes store if you weren't going to at least keep it in iTunes? It's just nonsensical.
And it's nonsensical for a very good reason: Apple doesn't want to sell you music that plays anywhere. (And just because you can make it so, doesn't mean they'll encourage it.) And people know it. By and large, when a consumer makes a purchase in the iTunes store their intent is to make the music available in iTunes, and then typically on their iPod. Not available anywhere, but available in iTunes - to do with as they wish from within the confines of what iTunes allows. Yes, it's a different paradigm than owning CDs or records, and it has different restrictions. But think about how little sense CDs and records made, in their own way: You buy this plastic thingy, so you can stick it in this other electric thingy, and then the sound you want to hear comes out. Lose either one and the sound is lost. Oh, and the plastic thingy costs 50 cents to manufacture, but by paying 15 bucks for it you're actually buying a license to hear the sound it makes and by the way the process of making an identical backup copy is totally illegal according to that license.
To make a long story short, "buy-burn-rip" is an inelegant backup method, yes - just like a VCR is a totally inelegant method for preserving your DVDs. You've gone and transmorgrified them during the backup process. Why? To what end?
"You might have the energy for that. I'll be backing up by copying files to a removable HDD."
Risky ... consider burning DVDs through iTunes 7's progressive backup feature. It saves _all_ metadata. Only took me ... let's see ... 29 DVDs to get it all (lossless ripping)! Then you can stick all those in a booklet and make a really awesome gift of them to a friend, on the condition that they return the booklet if your HD gets hosed. :)
"How can you get less hassle then buying a song from iTunes and backing it up?" : buy it, rip it, own it forever, play it anywhere.
You must realize that "buy it, rip it, own it forever, play it anywhere" is actually more of a hassle, and also misleading. Consider that if you buy music through the iTunes store, you effectively combine "buy it" and "rip it" into a single operation, and that "play it anywhere", of course, still applies. Your iPod goes anywhere. And you can burn a CD in the terribly unlikely event that you go somewhere and decide to play your music "out loud" and the device at hand does not have a line-in jack. As for "own it forever", look around you: Music containers are fickle. Where are the car 8-track players? The cassettes? The good sounding record players? How long before your vinyl warps and the tin in your CDs oxidizes? DRM workarounds notwithstanding, with digital music you have at least a chance of escaping this fate by making as many copies as you can afford, and moving them from device to device to device.
Don't get me wrong, I loved CDs in their day, I would spend weekends in Amoeba Records in San Francisco, and stuffed a 400-disc CD carousel with my prized collection. But for the past eight years that carousel has been inert, gathering dust, with the CDs trapped inside, because the instant I ripped them all in lossless format and hooked the computer to the stereo, that carousel became worse than useless: Now I can find the song I want in seconds, and have it playing instantly, et cetera. Truly a win-win-win-win. :D
Psst, wanna buy some CDs?