Tony did a great job and was very responsive so I'm thankful for that.
I also understand that it's hard to ascribe fault---is it the OS or your set up or the software itself? A function that was working fine and then just breaks on an update seems more black and white to me.
Then that gets you to when is it best to update? Naturally when there is the most downtime to allow for recovery in the case of problems. For me that's the weekend.
While I back up my build I don't currently have enough space on the host to create a checkpoint. With this experience I'll focus on fixing that fault point.
My business makes a physical object that I sell to other businesses. We mess up on occasion as all companies do. When we make mistakes we pay freight back and forth and replace the product. But I don't pay any downtime incurred due to the fault of my product.
I don't know what the standard is in the world of software.
Then I weigh it against $350 which as a business isn't that much to me in the grand scheme of things.