Same complaint here. I use an 80gb iPod Classic with an Alesis iMultimix USB8 live mixer to record performances at our local open mic. Starting in April, the WAV files from the iPod would automatically stream into iTunes when I connected the iPod, and it was a snap to select a whole evening's worth and convert the lot to MP3 to save archiving space (by a ton). Starting in September, I seem to have some kind of random corruption of these files.
Some hang up the program immediately upon being selected and the "convert to mp3" chosen from the Advanced menu. Others start to convert and then hang up, usually with 10-15 seconds left to convert. Others convert just as before without problems. I have had to force-quit iTunes a number of times to unlock the system. This is getting really old, and what was a semi-automated process has become one of picking through the files one by one, force-quitting when it hangs, then deleting the culprit when I re-open iTunes. I'm losing some irreplaceable recordings, which pretty much negates the whole purpose of capturing everything every week.
I don't recall when I made the last prompted update of iTunes, but it very likely could have been just before this started happening.
Another glitch in this recording method that's a bit off topic: there really should be a two-step procedure to delete a voice memo. More than once I have deleted an abortive performance, then recorded the next one. When I pause it and the menu comes up, it's easy not to notice that the selected option is still "delete". I make about 20 of these recordings every week, and it's my habit to select "stop and save" quickly so as to get the next one started. If we got a second screen asking if we're sure we want to delete, it would be easy to catch.
The voice memo feature is great, especially with a mixer than can use the iPod as a hard drive to capture live performances, but the software needs work!
