I don't know if you would understand this, but there are a near infinite and unpredictable amount of things that go wrong, especially with our servers. If I were to take your advice, I would have to make the updater, for every server, run mysql queries, server queries, a2s pings, profile requests and dozens of other checks. This would take near a minute for each server which causes more and more problems.
I'm going to lock this as we've internally discussed this topic to death. We're not going to have servers auto restart because there's always that chance of a false detection. You all would hate auto restarts and you would realize that the second it restarts and loses you money.