And if you know what you're doing, Linux never breaks anything.
I wouldn't necessarily feel comfortable making this statement. I've certainly had some bumps along the way over the years..and some caused by updates. However, it's been no more significant than the bumps along the way for Microsoft and 3rd party patches for my Windows servers.
Well I was referring to a base install if linux which is analogous to a base install of Windows. VERY basic tools and a default browser, nothing else.
Even basic installations of Linux include quite a number of apps in addition to what Windows provides. Usually components of Apache web server are there, components for Sendmail are there, there are music rippers, graphics apps like TheGimp, office applications, bit torrent clients, PDF readers, instant messengers, etc.
Even the slower release cycle distros still have a lot more updates than Windows does, including ones that break existing executables, drivers especially
Again, there are more updates.... I won't disagree with that. But it's also most likely updating every single piece of software on your computer as well. For example, it patches your OS, your browsers, your PDF readers, your office application, your graphics applications, your SQL servers, your multimedia applications, etc. The breadth of updates includes far more than you have with a Windows update.
The only real driver issues that I have had after an update are
1). for graphics cards. And that's usually just on machines with eye-candy stuff enabled. Most often, you also need to recompile the video driver against the currently running kernel.
2). For any other piece of hardware that I compiled a driver for. With these, you have to compile again against the newly running kernel (that's usually 2 commands, make and make install)
Note: for both of the above issues, on my production servers, I often exclude kernel updates from yum and rather evaluate the kernel releases to only get the ones that fix a major security problem or performance issue that we are experiencing.
The only way to keep a machine stable I've found is to simply never update it till you completely rebuild a new one. Course that leaves you open to attack vectors if you are running public servers so that's not a good option there.
I update my servers, running CentOS which are command line only quite frequently without issue. As noted above, I am more selective on kernel updates. Also, with proper firewalling techniques and so forth, and having very few ports open to the outside, you can effectively mitigate a lot of the security concerns anyway to the point where they aren't really an issue. For work, scanning with tools like Qualsys to see what security vulnerabilities exist based on how you are running can shed quite a bit of light on what you are vulnerable to and what you really need to secure yourself against.
I usually update my Ubuntu desktops at home every month or so and experience minimal problems when I update.
Linux breaks itself with updates CONSTANTLY. As a software engineer, even though I have the ability to fix it, it's a complete PITA to /have/ to constantly fix it instead of getting my real work done. The actual reality is, because you CAN fix/config linux, you pretty much HAVE to, noone else does.
I guess people just have lots of different experiences. I've got nearly 130 different Linux machines running in all of our data centers, test labs and such and we are a software development shop writing mainly webapps which run on Tomcat or Solr and we don't experience anything remotely close to constant breaking of our Linux boxes because of patching. And I have been supporting Linux servers for over 8 years professionally for multiple software companies. So, it's not like I haven't been around enough or set up anything complex enough to see issues.