I tried to switch recently, but eventually returned to Windows due to missing features/apps. I'll probably try to switch once again soon, taking the time to prepare some sort of dual-boot scenario. My desire to switch was primarily due to my increasing dissatisfaction with the "ecosystem" philosophy behind Windows 10 - and OS X for that matter. I don't wear tinfoil and don't really care if Company X indexes my email for targeted advertising, but I like to own devices of a variety of platforms, and prefer to seek cross-platform solutions. Also, I've noticed that even with all the "phone home" options disabled at install, the system has services which keep using bandwidth frequently even when the system is just sitting idle. Again, I'm not worried about security particularly, I am just beginning to be of the opinion that if I don't install something or turn on a switch to enable the system to perform a specific function (especially an online one), it shouldn't happen.
Upon installing Linux, however, I found that there were a variety of missing apps and features, and some quirky issues. I spent entire evenings working on solutions for one after the other, and I just don't have that kind of time. The application menu responded a bit sluggishly unless AMD's own gfx drivers were installed. Installing Plex was no issue, but using it was, because Plex Media Server requires writing permissions for a "plex" user for media files, and every time I would copy files over to the Plex media folders I would have to run chown/chmod to the files so that the software could use them. For reasons unknown, the file manager had no functionality for changing file permissions, and the applet for Users & Groups could only be used to view them, not change them. Okay, once that was set up, it worked pretty well, I just had to run a batch file every time I added more files. On the flip side, I could use Javascript to add a menu item onto a system tray icon to run it for me, which was amazingly cool. I was, however, less enamored with the way the entire screen would turn into a garbled soup of colours each time I disabled the HDMI-connected TV which acted as a second monitor for Plex.
Since iTunes cannot satisfactorily run on Wine, my AppleTV was more or less dead as far as streaming goes. I also could not sync anything onto my iPhone or iPad. These are not really Linux failures as such because Apple's system is extremely closed and it's difficult if not impossible to write apps to work with these devices. However, I doubt I am alone at owning devices such as these since there are no Linux streaming devices or Linux phones.
There are missing apps, however, such as no Evernote client, nor a Wunderlist client (lol... really?). Well there's a big part of my current workflow out the window, unless I can live with using the browser for them. I found three unofficial Evernote ones, two of which were discontinued and the third was a text-based console client that had to be compiled on the system manually, which I failed to manage due to it requiring an older version of some library. I also could not use my money budgeting tool, YNAB, because there's no Adobe Air support. (This may have since changed since YNAB has turned into a web solution.)
Even with these missing features, though, there is a great deal of freedom there. It was nice running a system that, when it was idle, it was actually idle. Also, font smoothing is still far superior on Linux and Mac - Windows looks terrible in comparison.