What the Hell – Using an iPod on multiple PCs

So I’ve complained a lot about Vista… and believe me I still have a lot of complaints.  But one of the biggest issues was getting iTunes and Vista to work together.  Which, while a hassle, worked.  (Now it works a little better because I got a Vista driver upgrade to my Razer Tarantuala keyboard which let’s me use the forward/back, volume keys, etc. more consistently while I’m in other apps.  So that process worked well.)

On the other hand, I’m not so happy with Apple right now.  They’re usually pretty good on the software and hardware fronts – and especially on integration.  I’ve got a few iPods – most of which are, honestly, collecting dust right now.  I use one when I travel, but recently I haven’t been travelling that much so I haven’t used it.  But on Friday we got an office for the game company and I’ll be spending most of my time there (as opposed to working from home).   More on this in a bit.

So given my large collection of music (mix of ripped MP3 files and iTunes purchases), I figured the easiest way to share them would be to use my iPod.  You would think since:

  1. The iPod is a hard drive.
  2. The iPod is authorized to play all the music.
  3. iTunes and the iPod generally work well together.

That I could just plug my iPod into my laptop and play my music.  Nope.  There are only three choices when I plug it in:

  1. Erase and Sync – basically make the iPod linked to this PC (which has no music).  not useful.
  2. Transfer Music – sync to this iPod.  I then have to authorize this PC with the iTunes store.  Not to mention it takes hours to sync during which time I can’t listen to my music.
  3. Cancel – this is dumb.  It shows my iPod in iTunes and I can see all my music.  But it is all grayed out.  WHAT THE HELL?

I might be wrong, but the experience I was hoping for was:

  1. Plug-in my iPod.
  2. It shows up in iTunes.
  3. I can play music from my iPod.
  4. I disconnect my iPod.
  5. I can’t play that music again until I re-connect it.

Now, I can play my iPod while it is sitting right next to my computer.  Where it doesn’t charge automatically.  Where the sound is not co-mingled with my PC’s sound.  It seems like this would be a common application for an iPod.  IMAGINE!  A mobile music library that I can play anywhere I want…. or not.

Wow.  That sucks.

Am I missing something or this just a horrible breakdown in the otherwise great iTunes/iPod ecosystem?

So, what do you think ?