Oddly, my experience is a mixed bag here. Teams I've been on that went for rigid standardization with docker have largely been much harder to upgrade than those that allow local dev however the dev wants.

This is subtle. There are more bumps along the way. However, the task of upgrading isn't neglected forever. Instead, it usually seems that each new member winds up upgrading some small piece and making sure the code works with a small change in environment.