Icloud errors not syncing songs ripped from CDs

I've been an iCloud customer since November 2011. However, since converting to iCloud the songs I've ripped from my CD collection nor songs (.aac) that were purchased from Amazon no longer sync.   iCloud errors out each morning, I'm asked to log off then back on (which I do dutifully) but the error continues. My music is flagged "Waiting" and so it does! Everything else works, which is totally aggravating since the problem is obviously itunes or a server side issues.
I've contacted support multiple times and the last "genius" stated that "I do not have the training or tools to assist you". That's about the nicest bugger off line I've ever heard!
Well months later and still no fix,  and the issue lingers. 
I was hoping soeone out there could direct me to a solution, contact, or a trueiTunes genius that could help..  Ill pay, I just want iCloud to work as it's designed to I'd be happy if it did that much!
Tom

I've been an iCloud customer since November 2011. However, since converting to iCloud the songs I've ripped from my CD collection nor songs (.aac) that were purchased from Amazon no longer sync.   iCloud errors out each morning, I'm asked to log off then back on (which I do dutifully) but the error continues. My music is flagged "Waiting" and so it does! Everything else works, which is totally aggravating since the problem is obviously itunes or a server side issues.
I've contacted support multiple times and the last "genius" stated that "I do not have the training or tools to assist you". That's about the nicest bugger off line I've ever heard!
Well months later and still no fix,  and the issue lingers. 
I was hoping soeone out there could direct me to a solution, contact, or a trueiTunes genius that could help..  Ill pay, I just want iCloud to work as it's designed to I'd be happy if it did that much!
Tom

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