iProducts were never subversive. I don't think the piracy explosion was either. Before Napster the only people sharing mp3s were people who would be trading tapes before there were mp3s , after iTunes caught on people sharing mp3s were people who would have been trading tapes before there were mp3s. In between, piracy was the way you got music in your preferred format. That wasn't subversive, that was being the most convenient option. But yeah, don't let Apple manage your music collection. Disks are cheap, and so is rsync.net if you want an offsite backup.
Did you price backing up the whole thing? You don't want to do that. At the very least you've mentioned keeping time machine backups there, and since snapshotting is built into the price there is no point in keeping anything but the most recent time machine image.
Synology will interface natively with Glacier, but everybody hates it (it doesn't do a good job). You can trick it into running Crashplan, but I haven't had much success (and backing up 6TB via cable modem is a drag). I'll probably buy another box, seed it locally and then try and use RSync over VPN to get it to update the distant from the local but I'm not there yet. After all, if the box does take a shit I'm going to want to be able to restore now, not at 10MBPS.