The certificates update every 30 days if you are running the NT Server app as an application. I ran the server app for 5 months with no need to manually update the certificates.
I changed the properties of the .exe to run only one copy, and then created a scheduled task than ran on login (that was set to automatic using netplwiz) as well as every 30 minutes. Just make sure that you set it to not run if an instance is already running. As long as the app doesn't generate any GPF messages, you should be fine, even when Windows Update requires a reboot.