I know you've all been dying to hear how my story worked out. I don't exactly know what fixed the issue, but I was finally able to get the new iPod software installer to bring up the window which allowed me to Update the software, though I first cleared the entire iPod. It took 80-90 minutes to reload the iPod with about 8500 songs. But, they're all there again!  

p.s. After googling "ipod help", I found a site which taught me how to run some geeky (used endearingly) diagnostic tests and such on the iPod, after one of which you could use some (or all?) of the buttons to play various sounds (like the click-wheel sound), including one that more-or-less sounds like a blaster from a sci-fi movie. Silly fun, that.

Re that John Gruber link ("Brushed Metal"): On the positive side, I still don't know a lot of the terms and references. On the negative: uh-oh, I understood enough to laugh and find the whole thing pretty damned funny. I think I may be becoming a geek. I mean, not that I have a problem with that. Do I?

Okay, so mine's a third generation iPod. Thanks for the elucidation. I've never seen one with a moveable wheel. Interesting.  

Of further interest may be my discovery today of just which songs are not being sent to my iPod: Those which I have bought from the iTunes Music Store. To add insult to injury, all of the iMS-purchased songs I *used* to have on my iPod have disappeared as well. I went to listen to High by the Blue Nile today, and surprise, it wasn't there, whereas Hats, for which I own the physical CD, was. And so it was with all my other purchased tracks.  

I've been an Apple fan back to the days of the Apple II, but they aren't earning any grins from me this week!

1G: the dial turns, the buttons press
2G: finger contact on stationary dial, real buttons in ring around edge
3G: buttons in row above stationary dial
4G: current stationary dial with integrated tap buttons

Software Update does not list any iPod updates. The Apple website had one though, which included software for the nanoPod, miniPod, and others, including one which looks like mine.  

I'm not sure which is the month and which is the date in Apple's numbering system, but I did assume that 2005-09-06 referred to three days ago, to coincide (exactly, or roughly) with the release of the nanoPod.  

By the way, is there a simple way to refer to my particular iPod? A quick glance at the pictures on the website makes it look like a "second generation" iPod, after the one with a thicker ring around the wheel (or something like that), but before the one with the four buttons at N-S-E-W on the wheel itself.

John Gruber's take on the absence of Brushed Metal in the new iTunes is hilarious.

Hmm, I just plugged in my 2G iPod for the first time after upgrading to iTunes 5 and got no error message, everything just updated like normal. If you run Software Update does it list any iPod updates?

I got the new iTunes, and now when I dock the old Pod I keep getting the message that "some of the songs were not copied to my iPod because the software on it is too old". So, I went to the apple website and downloaded 2005-09-06, installed it with (apparently) no problem, and still get the same message. During the installation process, the documentation suggested that when I next plugged in my iPod I would get an option to Upgrade or Restore (i.e. clear) my iPod, but that has not come up. I only get the same "some of the songs..." message. Is there something obvious I'm missing in terms of actually getting the software onto my iPod? I have the 40 GB version with a row of 4 buttons above the wheel, and my computer runs OS 10.4.2.  

And what the hell, I like the new iTunes look. (I hope that doesn't keep people from giving me advice here!)

You think that's petty, what's the deal with the sharpened window corners?

On a petty note, I was disappointed that they removed the brushed-aluminum look and replaced it with a matte grey.

Yes, the funniest thing to me about the improved control over randomness (and I'm an economist, so that makes me cringe) was that they were hyping this feature as a response to people who complained that random shuffle wasn't truly random. So to mollify those complaints, they provide a tool to *ensure* that random shuffle isn't truly random.  

Now that nano....well, my consumer impulses reared their ugly heads when I saw that.

Well, I didn't think of it as "trouble", since it doesn't require a reboot. It's a minor upgrade, but I like it. Mainly it's slightly better looking, the new Search Bar allows you to apply your search text to just artist, album or song names instead of everything (which has long been possible through Applescript, but they finally exposed it in the UI, following Mail's lead), and you can finally organize your playlists into folders (following iPhoto's lead). Some improved control over randomness, if that makes sense, too. Small features, all of them, but I'll use most of them, and it feels like they're consciously applying all the good ideas from each iLife app to the others, which seems like a Good Thing to me.

So, anyone downloaded it yet? I've read the list of upgrades, and nothing makes me think it'd be worth the trouble, and I'd love to hear what others think.