Hey Jerad,
Thanks and it's good to know that you're using staging. I've mentioned in my previous reply that I've checked our issue tracker and there is no report specifically a conflict with Jetpack. We also have undergone internal beta testing, user beta testing, manual updates and eventually, automatic updates.
What I was saying about Jetpack is, it's known to cause image issues. Maybe I should have added that it's not just in X but is also known to cause issues or conflict with other themes and plugins as well. It might also depend on the exact setup you have. There might be a combination of settings in your site that the rest of the users have not used yet that is maybe why there is no report yet.
We have pushed an automatic update because we see that there are no critical reports. But, we are always happy to troubleshoot any update issues and in fact, our development team is quite quick to fix the reported update bugs as you can see in our Release Notes at https://theme.co/apex/forum/t/release-notes-pro-2-3-x-6-3-cornerstone-3-3/44607
I would just recommend that once you found an update issue in your staging site, you participate in reporting the issue so that our development team might uncover something from your setup.
We try very hard to beta test our products before releasing but it is even harder to replicate each and every WordPress setup especially conflicts with other plugins. That is why, there are still new issues and sometimes is only uncovered when all users update and that is only possible via automatic updates.
And with automatic updates, we do understand that non-technical users like clients might push the update link or button so I'd recommend that for your client sites, you disable automatic updates. If you don't know yet, you can follow the link below which is a guide to do that. Just note that I don't know your exact scenario but just giving you an idea.
Once you've tested the updates in staging, maybe you can enable the automatic updates in your client sites or send them a go signal to update.
I hope that information is useful.