Honestly, linux hasn't been much better than Windows. linux just expresses its troubles differently. I'm in a tiny company and managing our company's little email and web servers is part of my job. All of that runs on linux and, most of the time, is wonderfully reliable. HOWEVER, every two years (I use Ubuntu LTS builds) there is a significant "upgrade" to the OS. Unfortunately, every single one of those has also included upgrades to various packages (like postfix, php, mysql, etc) that are INCOMPATIBLE with previous versions! When this happens, it can take days to figure out all of the adjustments that must be made to our configuration and, since everything is just in text files that I only look at every two years (because things work so well in between updates) I must re-learn amost everything every time I update. And yes, I've heard all of the scolding and comments about note-taking, etc., but when you have a boss and customers screaming at you to get a server back on line, good note taking is low on your priority list.
I don't run Windows SERVERS, but I have NEVER encountered such major incompatibility issues with Windows or software that runs on it. When a new version is incompatible with the previous, the upgrade clearly informs me and offers to automatically migrate my old configuration to the new while asking for any new settings required. linux may say there is a new config file that is recommended, but it won't contain any of your old settings if you use it. I'd be surprised if the linux desktop is any friendlier. By and large, linux is written and maintained by people who love computers and coding (and are VERY good at both) and they appear to expect that anyone using their system is the same (or at least wants to be the same) as them. IMHO, this is the biggest flaw in linux ever since the first time it was predicted to replace Windows. As a developer, I understand the nearly pointless task of writing a migration tool that will run only once -- but when it will run once for MILLIONS of users it becomes quite a bit less pointless, but still, very few of these are written for linux applications (at least, not for any of the server applications I've used for the past 18 years).
I, too, am against the pushy Windows 10 upgrade system, but I'm not sure where to go in a few years when Windows 7 no longer has working drivers for market hardware. Hopefully, something will be ready by then.