I ended up on a Windows machine for a couple of days, my Linux machine was inaccessible. I was using a Windows machine after a gap of about an year or so. My usage was limited to only testing on Windows specific applications.
I had to install a couple of applications to get my basic development environment up. And was that painful! I have got so used to the online repository way of installing applications that the Windows way of installing applications sucked most of the energy out of me.
Most of the Linux distributions have online repositories of software packages available. It is usually just one command or couple of clicks in the GUI to look for and install a specific package. It deals with dependencies, or at the least warns you about them gracefully. For example, on my Arch Linux machine I have to use the command
sudo pacman -S vim. These commands not only install packages, they can also seamlessly upgrade them or update your cache of the repositories. Also, unlike a lot of installations they also handle the uninstallation and downgrading for you. In fact, on Arch Linux, even my OS is upgraded seamlessly.
I will not say that the Windows way takes a lot longer, but it surely is tedious. So much so that sometimes it discourages me from trying out an application. Also, I find the whole Add/Remove programs unusable, especially because, you end up getting multiple entries for a single installation you did. Then there are also the Windows updates, but they have been involved more in creating problems than solving them.
Of course, there is an effort in maintaining the online repositories, and there have been problems in managing dependencies sometimes. But majority of the times it just works, and the problems have been handled by the community. There is also some work being done to improve compatibility across distributions. However, even today, the packages are created and maintained by the community. To some extent the community itself has retained the diversity, which perhaps shows that it is in response to what the user wants.
So what does Microsoft have to do to get something like this up and running? Windows has some good third-party applications, but they are hardly visible or accessible. These developers and the users both need this. But I do not think Microsoft will be able to do it. Not because it cannot do the design or the technology, but because it has not shown any inclination towards harnessing a community. And without community it will not work.
It is typically said that Linux asks its user to know a lot more about the system to properly use it. In this case though, I believe, the Linux installation is more intuitive and usable.