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I think I may have found the issue, though I ran out of time before validating a fix.
I had missed that in the "define service" from objects.cache it did not list servicegroups. That is the key difference. It seems that between expanding hostgroups and servicegroups I was overloading the environment.
First thing tomorrow I will try disabling enable_environment_macros and validating if any of our checks are relying on that.
Even if they are it should be ready enough to solve by modifying the checks to take them as arguments, and adjusting the command definitions to pass them along.
Just to close the loop, that was indeed the case.
Disabling enable_environment_macros worked to resolve the failing checks. And it looks like we have no checks that were relying on environment variables (which was as I expected).