Good point, but no. If you have architected your apps properly, decommissioning or sunsetting services or individual components should already have been designed and planned.
You really just don't have to think like this on the msft stack. I'm so glad I chose msft ASP 20 years ago, instead of php, or RoR or python, or node or any of the myriad other stacks that have come and gone since.
Do you ever need to update your servers to a newer version like say 2016 or now 2019? There are definitely issues on using say old VB6 libraries when you need to upgrade your severs from 2008 to 2019. Not to mention using those old technologies if you do have a new feature or change you end up with an unmaintainable mess. I am MSFT stack programmer, but to claim there are no issues and you just need to patch a server is flat out wrong.
I know, I know... It's almost never the case.