ITunes Match Syncing With Two Out of Three Devices

I use iTunes match on three devices, (1) a windows computer that is about 4 years old, (2) a Mac Book pro that I bought this spring, and (3) an iPhone 5. Before buying the Mac Book pro, the music library was created mostly though the windows computer, although I occasionally bought iTunes content on the iPhone 5. Everthing in the iTunes library -- purchased from iTunes, purchased from Amzaon, purchased from Bandcamp or ripped from CDs -- was available on the phone; everything purchased on the phone was available on the windows computer.
For the first several months of using the Mac Book pro for purchases (mostly outside of iTunes) or for ripping from CDs, all content uploaded through iTunes was accessible on the windows computer and the iPhone. However, sometime recently (I can't pinpoint the day), non-iTunes purchases and CD rips from the Mac Book and uploaded through iTunes Match stopped being accessible on the windows computer. There is no issue with the iPhone. All uploads are immediately accessible on that device.
I have checked all of the iTunes settings on the windows computer. Everthing is enabled. I have turned iTunes match on and off on that device, to no avail. One odd glitch is that "icloud status" is shown perpetually as "waiting" in the library on the windows computer. Again, though, the tracks shown in the library on that computer are only those that were either purchased on that computer, purchased from iTunes on another device, or ripped from CDs on that computer.
So it appears that iTunes match has been "missing" for a couple of months or so the windows computer as respects non-iTunes content purchased on the Mac or ripped from CDs with the Mac.
I am using all of the most recent software updates on the Mac and the iPhone and as respects iTunes. The windows machine uses Windows 7.
Any suggestions as to how to fix this? Thanks,

The iCloud status cleared. Thanks. But the iTunes Match items uploaded from the Mac are still not showing up in the library of the windows computer.  Everything is still enabled, but the synching between the Mac and the iPhone on the one hand and the windows computer on the other hand is still not working. And the match process on the windows computer took a couple of hours to complete, so it seems like something was happening. But just not everything.

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