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iTunes syncing drives me crazy

Couldn’t sleep tonight because of jet lag, so I tried to get iTunes libraries to behave as I want them to. Here’s the deal: I have an external hard drive that now contains all of my music - 200+ GB of it.

I would live to have a way to move some of it - usually 500 MB or so - back to the hard drive of my Macbook. Temporarily. To listen to while at work or about. But I want iTunes to keep track of the ratings and play counts of those tracks.

After researching pretty much everything on the subject, it seems clear there’s no way to do this. The two solutions one can use in the meantime are:

  • Use an alternative library with only the tracks on the laptop’s hard drive. This will not keep the ratings and play counts.
  • Use an iPod instead.

    • I also spent a long time looking at syncing solutions for calendaring. I need a solution that integrates with Sugar CRM via Thunderbird’s Sugarbird. However, for someone used to iCal, Thunderbird’s Lightning is quite uesless. I can’t believe it asks me to click on the “more” tab to get to where I can post a reminder - and even then, the “reminder” solutions are very poor. 

    OK, but I can use Google Calendar to sync between all of these systems, right? I truly love the iCal interface, so I want to keep that. I went to Spanning Sync - only to find that you purchase it for a defined Google Calendar account.

    But we’re also moving to Google Apps. Hmm… all in all, it’s driving me crazy.