D, I've got a 1 gig ipod shuffle I bought 3 years ago that's still working well. I've had to go through 5 pairs of headphones during that time but that's a separate issue. actually I've never needed more than that 1 gig at any point. I'm never more than a day away from my computer so I just load a playlist and go. 1 gig holds a lot especially if you down convert everything to 256kbps. foobar lets you convert FLAC to whatever bitrate you want pretty easily as you transfer onto the ipod.
I think as a general rule they're overpriced for what you get and compared to their competitors. but occasionally they have something that's a pretty sweet deal like the shuffle and you gotta jump on that. ipod classic seems like a good deal too if you need all that space, though it's a hard drive so I guess more likely to fail. still, a good price for what you get.
I don't think I could ever justify buying one of their computers - they're overpriced vs retail PCs which are overpriced vs building your own PC. unless you really need Final Cut Pro or something, I don't know of any other reason to buy a computer from them at this point.