If you really want to automate this sort of thing you should have redundant systems with working and routinely tested automatic fail-over and fallback behavior. With that in place you can more safely setup scheduled maintenance windows for routine stuff and/or pre-written maintenance scripts. But, if you are dealing with individual servers that aren't part of a redundancy plan then you should babysit your maintenance. Now, I say babysit because you should test and automate the actual maintenance with a script to prevent typos and other human errors when you are doing the maintenance on production machines. The human is just there in case something goes haywire with your well-tested script.
Fully automating these sorts of things is out of reach more many small to medium sized firms because they don't want, or can't, invest in the added hardware to build out redundant setups that can continue operating when one participant is offline for maintenance. So, depending on the size of your operation and how much your company is willing to invest to "do it the right way" is the limiting factor in how much you are going to be able to effectively automate this sort of task.