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If you are a system administrator, you should be pulling RSS feeds from sites like Secunia, which should let you know way ahead of time if your distro is going to be pushing some patches. Unfortunately, the task of knowing what is broken falls on you, not your distro package manager, especially if your systems support programmers.
Where I work we have a pretty extensive process that involves using software called Patch Link to notify us of the most important security related updates, and we apply them after testing, on a package by package basis. If you only have two servers the process should be much simpler.
It would be prudent to ensure that your testing sever is kept upto date and any packages that have bugs affecting you and your servers should be kept up to date.
I use VCS on my /etc/ dir as well to ensure that any config file changes can be seen with a 'git diff' command.