Though, to be fair, even as a Windows user and relatively firm fan of Windows, that happens for me routinely on Windows. Windows Update in particular is confusing with its many error messages that either magically resolve themselves if you retry enough times or require significant and arcane manual resolution. Managing home network file systems and printers with Windows in 2016 seems basically unchanged from 1998. Microsoft added "HomeGroups" to make this a bit easier for lay people, but they have more or less abandoned to its Windows 7 iteration, with virtually no evolution since. Now they channel their efforts toward integrating their cloud storage services.
Generally speaking, this is the trouble with general purpose computing and general purpose operating systems—there are rough edges and a huge number of corner cases that get ugly. In several decades of evolving these systems, we've not buffed those rough edges down as much as we'd like. It's similarly the reason mobile operating systems are popular for primary computing devices for a growing segment of the population. (Although, I will add that mobile operating systems are picking up the same rough edges as their capabilities expand to encompass more of the terrain typically associated with general purpose systems.)
And that's true across most operating systems. I recently upgraded my Dell tablet to Windows 10. Oh the humanity. And with every OS X version, problems with my 2009 Macbook are increasing, especially in the first few iterations.
Apple's post-90s hardware selection scarcity is a boon for them, as you don't really need to check that many configurations. Similarly, running Linux on slightly older Thinkpads is usually a very good bet. Doubleplus that if the wifi card is either libre enough or is replaced with one that is.
But as I'm not doing the hyper-mobile thing (I don't work from a beach or cafe and don't even like conferences), a desktop is usually the best choice for me. Cheap, fast and you can build one with fewer faulty components.
Originally left it to upgrade overnight, only to come in the morning (this is on my work machine) to see that it hanged somewhere in the process and wouldn't move on without user input. So I proceeded with clicking through all the prompts, and when 14.04 first loads, it's SO SLOW. Long story short, it took me 4-6 hours to finally get it usable. The whole time I was thinking, "how could they mess this up so badly?"
The host OS for the VM is Windows 7, and I have to agree with the author, it is much better to use. I only run the VM for the command line, but may upgrade to Windows 10 when Ubuntu on Linux comes out of beta this summer.
At the end of the day, I just don't recommend people switch to Linux.
It's basically because of Mageia that my linux hand-editing config know-how has atrophied down to nothing.