If you're talking server to server. Linux distros as servers go have always been headless (no gui), but you certainly can add a GUI or admin them through a lot of web based tools like WebAdmin. Windows servers have mainly been with a GUI, but with newer releases 2016 and 2019 you can also run them headless or chopped down. You can manage nearly anything through the server GUI if there is one, through the Server Admin Console on another computer or server, through Powershell or their newer Windows Admin Center which is web based. I've managed plenty of both Windows and Linux systems and don't really find either one more challenging. They just have different commands and different ways to represent things.
Everything in Windows is an object and everything in Linux is a file. Besides that they are very similar.