Dave, what you're talking about there is what I described in my second paragraph in post #3, which I agree works more often than not, as I said. But I don't think he's trying to play the external sound (XM2 in your case, SK1 in his case) from the controller, I think he wants the transpose button on the controller to alter his SK1 so that the SK1 will be similarly transposed when it is then played from its own keys. That won't work (and obviously wasn't a factor with your XM2 which didn't have its own keys in the first place). Maybe it could work if there were a way to program the controller to send sysex to the Hammond when invoking its own transpose function, but the Grandstage itself cannot do that.
This is based on my interpretation of where he said he "would like to transpose both keyboards." But if indeed he actually meant that he wants to play the sounds of both keyboards from the keys of the Grandstage (where the SK1 will stay in tune with whatever transpositions he invokes on the Grandstage), then yes, there is a good chance that will work fine.