I just purchased Kelly clarkson Greatest Hits and Carrie Underwood Blown Away CD's from iTunes, and I am getting a message that these are "Inelegible" to be uploaded to iCloud. Does anyone understand why a purchase from iTunes would be inelegible to be uploaded to my account?
You need to distinguish between songs you bought from iTunes and songs you ripped from CDs which are not available in the Store.
When you purchase a song in the Store, you are allowed to re-download it to your other devices. There's no need to upload it - you would simply be duplicating material which is already online, and if everyone did that it would waste a huge amount of storage. If you have a song, taken from a CD, which isn't in the Store, then obviously it needs to be uploaded before you can download it on other devices.