When I use Sync My Itunes I always get the message that Itunes is busy and to try again later. I'm trying to sync my Touch so I don't get the index is full message. Help.

Question

I'm trying to use "Sync My Itunes" to use my Ipod Touch in my 2011 Ford Escape.  I keep getting an index is full and all songs may not play message.  When I use the "Sync My Itunes" I always get the message that Itunes is busy and to try again later.  How do I get this to work?  I can't reset my Ipod without losing all my 4,000+ tunes.  Help!

Answer 1

The "Show iTunes in the Cloud Purchases" solution did not work for me, but this did:
In your iTunes library, make sure the "iCloud Download" column is showing (looks like a little cloud icon). Check for any songs that have a light gray cloud icon. Do whatever you need to do to make this icon disappear for that song (get iTunes to make sure it's downloaded onto your machine, or delete the song). Run Sync My iTunes again and it should finish.
Notes:
- Plugging in your iPhone/iPod might cause these songs to get copied back into your library, and you'll have to do this again. 
- I didn't start having this problem until I bought Match
How I discovered this:
I noticed that it stopped every time at song #1242 in my library, so I ran "Sync My iTunes (Debug)" to see which song it stopped on. Then I went back to my library, found the song, and noticed it had the light gray cloud icon. It also had a local copy of the song already. I think iTunes gets confused sometimes and forgets that it downloaded a song from your cloud library, then tries to download it again even though it's already on your computer. Then it realizes the file's already there, and doesn't download it. However, it leaves it in your library flagged as an incomplete download. Sync My iTunes triggers iTunes to attempt download, which then makes it look like iTunes is busy. My theory at least...