I am using the latest Windows version of iTunes (6.042) under WinXP SP2. Apart from those of you who are going to advise me to deal with my frustration by moving to Linux or MacOS, I am interested on feedback on the following scenario.

My iTunes library is around 6000 songs. Recently, I found a wonderful program that satisfied my obsessional needs to attach album art to each and every cut in my collection. The latest version of this program, iArt, has the added ability to go through my library and build a list of those songs which have multiple pieces of artwork attached to them, which is an annoying problem with iTunes that needlessly increases the storage space of the songs both on my desktop computer and on my iPod. So I went through that list and deleted the extraneous duplicate artwork. It turns out that 1800 of my songs had had multiple pictures attached to them (!), so I ended up saving between 2-3 gigs of space on both my hard drive and my iPod.

And that was where the problem began. I have my iPod set to auto-synchronize every time it is plugged into its cradle. But despite numerous attempts, with reboots of both the desktop and the iPod, the attempt to update more than 1800 songs would crash somewhere around the 700th file, giving me a message along the lines of, “The instruction at xxxxxx referenced memory at yyyyyy. The memory could not be ‘read’.” One of the problems was that, with the synchronization process crashing, those 1800 songs were erased from my iPod (or at least their index entries were) and, no matter how I tried, could not be resynch’ed onto the iPod.

To jump to the punchline, I finally solved this by changing the synchronization method from automatic to manual; building four or five playlists of around 400 songs each from the group of 1800 (fortunately, you can sort your iTunes library by last modified, so all the songs whose artwork I had modified last night were grouped together at the top of the sort), and synchronizing the missing songs by dragging these smaller playlists onto the iPod one by one.

So the problem was solved (the only abiding annoyance being that, after I changed back to automatic synchronization, the blinking “do not disconnect” message on the iPod screen now never goes away, even when synchronization has completed, until I reboot the iPod), but it leaves me with three questions. (1) what would someone have done who knows less than I do how to problem-solve such a scenario? I wouldn’t even bother calling Apple phone support (or any other phone support, for that matter), since I know all they would have told me would be to uninstall and reinstall iTunes; wipe the iPod clean and start from scratch; and finally, if that didn’t work, to reinstall Windows XP. I was worried about wiping the iPod and starting from scratch because it seemed that this was an issue of iTunes’ synchronization system choking on a certain volume of data, and of course I would expect it to choke around 700 songs if it were trying to transfer my entire library. One can never get access to anyone by calling tech support who really knows the innards of the program and can talk as intelligently as an intelligent and curious consumer would like, it seems to me.

(2) What woudl someone have done who knows more than I do how to problem-solve such a scenario? Some of you readers out there must have some thoughts, or even some similar experiences.

(3) Why does this particular Microsoft error message put the word “read” in quotation marks? What exactly is so ironic about the concept of trying to ‘read’ memory??