This felt like a better fit here than ServerFault.
I am currently migrating a server from Windows Server 2008 to Windows Server 2016 (those details aren't terribly relevant). "Pretending" that no one knows what is installed and in use on the old server, what do you look at to know what needs migrated/installed/configured?
My list so far:
- IIS 6/7
- HOSTS file
- Scheduled Tasks
- Local Users
- Installed applications
Obviously, we'll test the new server before rolling it into production, but if I can catch anything early, that would be great.