Mmmh, point taken. I only had problem with updates on Linux when I was using Gentoo and lived on the unstable branch (and unstable, of course, implies that such problems are to be expected).
There is a difference between administrating a single machine at home, or maybe a handful, or taking care of a company network of (in my case) about 80 machines (and that is still a tiny network, I suppose). Problems that a typical user only sees once in a couple of years become disturbingly common as the number of machines grows, and I guess that is true regardless of the operating system being used.
Having said that, I have encountered some rather strange and frustrating problems with Windows updates. One time, a Windows update would somehow not successfully register itself as being installed, but it did require a reboot. So after installing the update, the user rebooted her system, finding yet another update (the very same, in fact) available, install it, reboot, find another update... For some reason, only two machines in our network were affected by this problem, and I have no clue why it was these specific machines. One time, an update to Office 2013 overwrote some VB script that Autodesk Inventor happened to depend on, causing it to crash while displaying the splash screen; reinstalling Inventor hepled with that, but now Outlook would crash when trying to write an email. Another time, an update caused a few machines to hang while booting. There was an update to Windows 8.1 that was not called a Service Pack, but for all intents and purposes, it was, and Microsoft said that without this update installed, 8.1 machines would no longer receive updates; however, this update caused 8.1 in combination with a specific version of WSUS to no longer talk to the WSUS server - I think this is what people call a Catch 22.
And the list goes on and on. I have only a few years of experience taking care of a relatively tiny number of systems. Like I said, I understand now why large companies run labs where they test Windows updates - and updates by other software vendors, too, I suppose - against each and every combination of hardware and software being used on the corporate network.
Just because you did not run into problems does not mean there are none, just as my experience with updates on Linux and FreeBSD is not representative of what it is like to run dozens or hundreds of machines with these operating systems. However, currently the operating being used on the majority of company networks is Windows, and the company making billions of that is Microsoft.
Although, to be fair, in many cases where an update to Windows breaks a third party application, I suspect the third party is at least as much to blame. In my case, I have grown very weary of Siemens automation software (Simatic, WinCC, TIA), which is very sensitive with regards to updates, to say the least. So, to a degree, Microsoft has merely become a victim of its own success.