I think the toughest thing for me has been watching my former coworkers on Windows transform from technology loving builders into depressed cynics. Like these were some of the most brilliant people I knew and now they struggle to get out of bed.

100% agree, I still can't believe how fast windows is deteriorating. With that said, Linux and Debian helped me a lot. I enjoy tech again. With windows I hated 95% of changes, with linux it is the exact opposite. Having some experience since Ubuntu 12.04, it's amazing to see the progress especially of the last 5 years.