If you want Windows boxes to stay updated then have a way to replace the entire machine and replicate all needed application data (including sql server database

If you want Windows boxes to stay updated then have a way to replace the entire machine and replicate all needed application data (including sql server databases and anything proprietary) within minutes or hours at no notice. The Windows Update Service is a practical nightmare. It will get corrupted. It will require an entire re-image of the machine to fix. It will happen on production servers and client endpoints without regard to core business impact. It might even happen at a rate of a few per hundred of installs updated.