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According to Troubleshoot stopping your instance:
"If you have stopped your Amazon EBS-backed instance and it appears stuck in the stopping state, there may be an issue with the underlying host computer."
I don't remember a time when you could change the instance type of a running instance, you have to go through the stop-change-start cycle.
You can also setup the auto recovery option on your instance, Recover your instance
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Thanks @kentrad! That auto recovery seems like the perfect thing for this mission critical server. I'm going to set that up!