Moxie I have been using FireDaemon since nightrider suggested it and it's a pretty good tool. You can also get FireDaemon Fusion which is a free tool to allow you to manage the services remotely.
I also replied to your question about Auto update with FireDaemon in the Auto Update thread a few days ago:
http://forums.alliedmods.net/showthr...=170532&page=8
Like I said we still need to wait for an actual update from Valve before we can fully see if it works, but from what I see when the server crashes/starts it runs the updatetool with no problems.