Agreed on iRiver. Their players were so much better than Apple's for one or two generations, and then they degraded rapidly. I can't imagine what went wrong there.
I soooooooo wish I hadn't sold that on eBay.
I was referring more to software design. I have never encountered so many plain boneheaded interface decisions as in Microsoft products, from roughly Win95 up to and including WinXP. I'm not even talking about ugly (which I can forgive), I'm talking about simply unusable - tiny text areas without scrollbars in which you sometimes have to input a large amount of text, or worse, text inputs instead of text areas. Tabs being used where they really shouldn't, resulting in dialogs with up to 5 rows of tabs, and with extra "Advanced" buttons on some of the tabs that bring up another pop-up. That kind of stuff. Vista and the new Office have been really pleasant surprises so far in this respect.
Good design is strangely lacking in the tech industry. Sony has it (sometimes). In the mp3 player area, IRiver had it (briefly), but it wasn't enough. When looking for a laptop recently, I was dismayed at how plain bad most Windows laptops look (for the record, I ended up choosing between a Dell and a Sony, and went with the Sony because I didn't want to wait 2 weeks). Microsoft is a consistent case study of how NOT to do design. Whatever else Apple might do wrong, design isn't one of them.
Let me put it another way. If the auto world only gave you two choices - '88 Ford Taurus knock-offs and Lexus - I'm willing to bet Lexus owners would be a lot more fanatical.