Why is deploying software to remote computers so challenging?

It seems that with 90% of the software (current software that companies still make, modify and sell) I have to install for computers, there's always a huge challenge trying to figure out how to deploy it. Most software I can throw a switch at the end of the exe or MSI to make it silent, or include the license key, but it seems like most software creators or packagers do not think maybe more than a few people at a company will need their software installed.

I'm not a fan of "recording" packages and deploying those, Microsoft advised that's not a good practice.
Why can't they just include a switch to make it easy to install something from the command line? I understand some software is more complicated, but the ones where you just click Next a couple times, select all features, enter a license key and finish, why's it so hard to allow customers to automate that?