Automatic download issues

I am having major difficulties getting iTunes purchases to automatically download to my iPod touch or iMac.  I've checked to make sure all settings are correct and then made a few purchases on each device.  For example, I click the following on my iPod:
1. iTunes
2. Purchased
3. Music
4. "Not On This iPod"
The result is a message that says all my available music has already been downloded.  However, this is not accurate; I have three purchases on my iMac waiting to transfer over.  I also have a purchase on my iPod waiting to reach my iMac, but again, to no avail.
To the best of my knowledge I have set everything up properly, however I'm sure it's possible I'm missing something.  Anyone with similar issues who has found a resolution, please share!
iCloud seems like a great idea but of course, only if it works!  Contacts and calendars are syncing up just fine, now I just have to get my music to do the same.
Thank you kindly in advance.

Funny but I just received this email from Wired that had a highlighted section about automatic downloads.
The only problem is that when you go into the App Store tab there are two interfaces for Automatic Downloads. There’s one under Automatic Download for all Apps and a specific one for Wired magazine to automatically download new content when on Wi-Fi.
So the question I’m facing is, do I need to have Automatic Downloads for all Apps on as well. Unfortunately the notification from Wired is a bit ambiguous.

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