Just for you info, I have about 6,000 songs on a 32 gig thumb drive and none of the songs are in the root directory. They are all in the folders that iTunes puts them in. I just copied directly from my laptop hardrive to the thumb drive and it works perfectly with Sync.

Are you sure your external HD was formated FAT32?

 

Yes, the hard drive can have a file structure with folders as long as you only have audio files on it. I have an 80GB Ipod Classic with 4000 songs on it and it works great. My iphone takes about 5 minutes to index and never finishes correctly. I only have about 2000 songs on it. Using Bluetooth to stream the music works great but than you have no titles.

 

I have a 30 gig iPod Touch and it only took a few minutes to index and did not miss any songs. I would get in touch with the dealer. What you are experiencing is not normal.....

 

Hmmm... interesting. Yeah, it was/is formatted in FAT32... I am about to go out and try the drive with songs in the root directory, will report back soon.

 

Well it works now! I reformatted in FAT32 using command prompt instead of some program (Vista doesn't like FAT32 on 32g and higher) and I also put the songs at the root directory. Turns out I may not have had to do that, but I can fix that stuff later. I appreciate all the help.