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David,
If you could ensure enough rigidity to eliminate differential flexure, and guide off say a OAG on the longer focal length scope - you could reasonable expect to take two shots at once. Given the differing scopes would have differing magnification and fields of view - doubt you could readily stack the shots across different OTAs though.
Also aligning the scope perfectly might be challenging if one is a SCT - their mirrors tend to sag slightly as you point them across the night sky.
Maybe borrow some gear and give it a go - or ask someone else to try it for you?
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