I had this happen yesterday with my iPhone 4 so don't feel lonesome.:)
I was getting iPhoto to start up but iTunes was not seeing the iPhone.
So I restarted the iPhone then did a Restart of my MacBook Pro.  The current 
version of iTunes has a few bugs
That I have noticed.  The drag and drop of album art is one that shows up a lot 
and it is back in the latest version.
There will be an update to iTunes when the next iPhone comes out and I hope 
this bug goes away.
The album art bug is one that drives me crazy an I like high rez. art  in my 
mp3 files tags  where talking 1500x1500.
To get around this bug of dropping the art on to the info window of the album 
select. I found that you can select a  whole album in
List view then drop the art in the album art window at the lower left hand side 
of itunes this will copy the art to the Tag of each mp3 file.



From: [email protected] 
[mailto:[email protected]] On Behalf Of Alex Whitman
Sent: Friday, August 05, 2011 9:55 PM
To: Macintosh topics
Subject: [MacGroup] ancient iPod: that syncing feeling

I have an iPod from 2003 or maybe 2004, the 3rd generation, with a touch wheel, 
4 buttons and a firewire dock. Today I tried to sync it with iTunes (10.4). No 
dice - iTunes becomes unresponsive and gives me a spinning beach ball until I 
force quit. The battery will charge but there is no syncing happening. Tried it 
without the dock, just the cable, with the same result. This is the first time 
I've tried to sync it in at least a year, so several iTunes updates have 
happened since then. Is it simply obsolete? Or is there something else I should 
try?

Many thanks,
Alex
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