On the other hand, every time I've been in an "update everything constantly" situation there have been extremely painful outages every 6 months because people p

On the other hand, every time I've been in an "update everything constantly" situation there have been extremely painful outages every 6 months because people put dramatically too much faith in their unit tests to make updating "quick and painless". Personally I go for having a recurring calendar entry every few months that blocks off a few days to very carefully read all the patch notes before updating