It has been requested, by the community, to have the option "Install and Restart" option on the Shutdown Event Tracker on Windows Server, however never implemented.
Technet@Microsoft says the following of the Shutdown Event Tracker:
Shutdown Event Tracker is a tool that prompts users to record a reason why they restart or shut down the computer. This information is available for review in the event log. If a computer running Windows 7 is connected to a domain that uses monitoring tools, you can collect this information as part of network reporting.
When Shutdown Event Tracker is enabled, users cannot shut down or restart the computer without providing a reason. If the computer is shut down or restarted unexpectedly, either as a result of power interruption or hardware failure, the user is prompted to enter a reason in Shutdown Event Tracker when the computer is started again.
Thus it is possible to Disable the Shutdown Event Tracker, if one likes too (and it gets to anoying in a development environment). Or even better - you can add your own Custom Option to your Shutdown Event Tracker if you like.
Why "Install and Restart" isn't listed as default, is hidden within the guarded walls of Microsoft fortess I'm afraid. But hopefully you'll get your own custom option up an running in no time.