Not able to manually add music now that I've got icloud and match.

Now, when I attempt to drag and drop, I get the red circle icon and am not able to put the track on my phone. Curiously, I am still able to drag and drop with my ipod nano.

Yes, if you use match then you can't sync in the old way any more on that device.
If you haven't enabled match on your device then you can still sync the old way. That's why you can still do so with your Nano (which of course can't use match anyway).
If you were to disable match on the other device then you would be able to drag and drop again, but wouldn't be able to access your cloud library.

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