The amount of times my Windows installation(s) broke is just as high as the amount of times my Linux installations had issues. The article you quoted seems to be from someone with more Windows experience than Linux experience.

One example: FileZilla is a capable GUI SFTP and FTP client, but so is nearly every file manager. I can drag and drop files from Dolphin into a fuse mounted FTP, SMB or SFTP folder just fine. Skill issue?

EDIT: omg, I just realised they use WinSCP for deploying applications. It really seems like a skill issue since you can automate that even without proprietary clouds. I can probably replace this person with a PowerShell script, which is even more efficient than them doing their job on Windows.

All operating systems sadly need lots of maintenance nowadays. The main reason I use Linux is that I feel in control of the system and the vendor doesn’t actively try to fuck with my installation.