I helped a friend out a while back and she hooked me up with a black iPod Nano 2G yesterday. I've love being 'paid' with gadgets. I've got an older 3rd-gen iPod 15Gig so I figured it'd be interesting to see how iTunes plays with two iPods on one machine. 

Here's what happened:

• Downloaded the new iTunes 6.01 and installed it on my laptop.
• Plugged in the Nano and was told after some thrashing that "an error occurred while installing your hardware. It may not work."
• iTunes noticed it though and started it's "What's your iPod named" wizard. I set it up as Scott's Nano and told it to "automatically update with Music."
• I've got certainly MORE than 2Gigs of Music so I was interested in the Shuffle-like "figure it out and give me some music" features. Apparently I'm an idiot or these features don't exist.
• After some churning iTunes reported that my iPod didn't have enough room for all my music. Not sure why that wasn't obvious since iTunes knew (via it's icon) that it was a black Nano.
• It offered to make a Playlist with "a selection of music" from my Library. I naively assumed this was the shuffled pile I'd been hoping for.
• It made a 300 meg list of music, mostly stuff I'd listened to often or recently. 300 hundred megs you say? That's weird. No warnings, no log, no logic, nothing.
• Turns out that it assumes you want ALL your podcasts by default. That was 1700 megs for me. I had to manually select that I just wanted "checked" podcasts and had to cull that list.
• I also told it to sync my photos, my calendars and my contacts.
  • Interestingly there is NO error message when you have > 1000 contacts. This is a known limit, but there's no notification. The contacts just don't show up. LAME. The interface is a single checkbox.
  • It syncs EVERYTHING in your calendar for all time, in both directions. This makes the calendar interface on the iPod VERY crowded and almost unusable as I've got 801 appts in Outlook as of today.
  • It automatically assumes that you want music first and photos, contacts and calendars last. So, if you fill it with music, you get no contacts, photos or calendars. You'll only get a warning if the photos can't fit.

I'll I want is to say:

• I want 1.5 gig of music, randomly chosen.
• I want the rest for photos, but I want ALL my contacts along with 6 months of appointments.

I fought with this interface for an hour last night. I don't know what's happening at Apple, and I'm just a caveman, but do I know this:

• iTunes 4 just worked.
• We went from v5 to v5.5 to v6 now v6.01 in the space of a few months.
• Something is seriously wrong in v6 that makes USB connectivity questionable at best.

My conclusion: If you have more music than your iPod can comfortably fit, you're going to fight with the space management aspect continuously.