OK, so I've been reading up on this, tried all the troubleshooting, etc., so don't flame me for simply venting my frustration.
I've created a brand spanking new Library (i.e., no media in it whatsoever). Turn on iTunes Match, all my songs in the cloud pop up. Lovely.
I attempt to add two songs to my Library, done. Update iTunes Match. Step 1 goes smoothly. Step 2 goes smoothly (most of the time, sometimes it will immediately reset itself back to Step 1. Step 3 is where it locks up, turns gray, and restarts at Step 1.
So, I try just ONE song, same thing. Seriously, I could build a better "Cloud" than this if I had the resources Apple has.
The purpose of this post is that hopefully SOMEONE at Apple will pay attention and resolve this, since I'm spending $25 on a service that doesn't function as advertised, plus an additional $20 a year for an extra 10GB of storage in this phantom cloud.
Oh... and here is what is showing up in the Console logs:
12/6/12 1:14:15.457 AM iTunes: _NotificationSocketReadCallbackGCD (thread 0x7fff78130180): Unexpected connection closure...
12/6/12 1:14:16.613 AM mdworker: Unable to talk to lsboxd
12/6/12 1:14:16.617 AM mdworker: Unable to talk to lsboxd
12/6/12 1:14:16.676 AM sandboxd: () mdworker(14992) deny mach-lookup com.apple.ls.boxd
12/6/12 1:14:16.681 AM sandboxd: () mdworker(14993) deny mach-lookup com.apple.ls.boxd
12/6/12 1:14:17.000 AM kernel: Sandbox: sandboxd(14994) deny mach-lookup com.apple.coresymbolicationd
12/6/12 1:14:55.578 AM com.apple.usbmuxd: SCEDeviceSocketCallback 0x102002890-ath/com.apple.AirTrafficHost remote peer closed connection for sce 0x102002890.
12/6/12 1:15:03.880 AM iTunes: _NotificationSocketReadCallbackGCD (thread 0x7fff78130180): Unexpected connection closure...
12/6/12 1:15:06.310 AM com.apple.usbmuxd: SCEDeviceSocketCallback 0x10020d840-ath/com.apple.AirTrafficHost remote peer closed connection for sce 0x10020d840.