This page of info seems to have changed recently, or else I'm just dense.
I, too, am having problems with songs into the cloud. In my case, I'm generating the song files and putting them into iTunes from GarageBand. Most of them upload into the cloud in some mysterious manner. I don't do anything special, they just are there, and I can listen to them on my iPhone. But occasionally, a file just doesn't make it. How do I FORCE a file to rise up into the cloud?
Also, every so often, a double cloud icon appears with a note telling me that there is a duplicate file so it gets confused and/or confusing.
Is there a sure-fire way to manage that which I wish to send into the cloud and keep locally that which I don't wish to fly into the cloud?
In other ways, the cloud seems poor for managing songs by other criteria. How does one cause the ORDER of songs in an album to stay where you want them?