We have looked a lot into different strategies, and methods for hardening images.  Do you think there is a better way to implement

Part 1: Question

We have looked a lot into different strategies, and methods for hardening images.  Do you think there is a better way to implement the CIS or STIG requirements that you have read through? What types of automation or machine learning could be leveraged to deploy these? Is using technology to secure technology a good thing or a bad thing?

Part 2: Use Case

It is your first day in the IT Security office of this awesome job you landed as a security analyst and helpdesk support technician. Your new manager has tasked you with assessing the current benchmarks that they have used for their Windows 10 images and to provide a report on actionable updates, threats and paths to secure their images. You have not been given any other information other than the above. What questions do you need to ask to be successful in your first assignment?