In my experience, even MSIs can be run from the command line, but the amount of effort required to look this up and write a clean script is definitely way more

In my experience, even MSIs can be run from the command line, but the amount of effort required to look this up and write a clean script is definitely way more than the equivalent Linux sysadmin task because Windows is just not expecting users to work this way at all. My gripe with installing things on Linux is that every project assumes install means “build from source”, and it’s often annoyingly hard to find the exact yum/apt-get name for something (do I need a PPA? is the name thing, libthing, libthing-dev, libthing2, or something else?) But this is a much smaller issue than anything I run into with Windows Server.