I've been using Windows and Mac concurrently ever since getting the 2007 aluminium iMac. Which is still, somehow, working fine albeit a bit slow. My current PC is one that I built myself back in 2011. I think the difference between operating systems is not as big as you think it is. Maybe it depends on how tech-savvy someone is or isn't, but Windows 7 has almost never caused me a lot of trouble. Not a spotless record but nothing that a bit of Googlefu couldnt fix. Hell, the only virus I ever got was incredibly lame malware on my Macbook Pro. I'll grant you that user experience design has been much better for much longer on OS X but even that advantage is slowly being eroded. (Case in point: iTunes.) In that respect I even think Android has surpassed iOS.
Know what's even worse than iTunes? Music in iOS. It constantly forgets what I was listening to. Queue up a couple albums, stop listening to music, then go back and find "Up Next" empty. I think it stores the queued music in active memory, so after a while the OS drops that. I went back to my iPod Classic, because at least that remembers what I was doing.Case in point: iTunes
Back at the birth of the web, I had three computers on my desk: a Sun UltraSPARC, a Mac, and a Windows box. I was doing testing of 3rd party Java and JavaVM implementations for JavaSoft (aka Sun Microsystems), and used all three machines heavily. When I moved overseas, eventually I had to replace my Mac and the closest Apple dealer was 3 countries away, and Apple was still charging 3x premiums for Macs overseas. So I switched to Windows at both home and work. Did that for 5 years or so, until I went back to the states and bought a 17" MacBook when it first came out. When I started this new job back in April, I started off on a Microsoft Surface with Windows somethingorother. The hardware was shit. The OS was shit. This company is an all-Microsoft shop (except the Executives, who are all on Macs, as is most of Marketing and about 1/3 of Product Development), so Microsoft Office, Microsoft OS, Active Directory, Outlook, the whole shebang. Every time I unplugged the Surface and plugged it back in, it would get confused about my monitors, and I'd have to constantly manually reset all my monitor settings. My MacBook Air connects to the exact same monitors, and works every single time. Often when the Surface would go to sleep, something weird would happen. It wouldn't wake. It would wake but never see my external monitors. It would wake and immediately crash. Or I would go to wake it up, and it would act like it had never been turned on before, and ask me to configure my language settings, etc. This was over 3 different Surfaces, so I finally asked for this old MacBook Air they had sitting in the corner, and I have been working on it fine ever since. Same work, same job, same software, different experience. I'm not saying you are wrong. This is just my personal experiences with some different OSes over the last 3 decades. (Then there was the other operating systems... BeBOX, Unix, Xenix, NeXT, PalmOS, WebTV, etc....)
Know how to run 3 monitors on a Mac Pro? Connect four monitors. Know how to run 2 monitors on a Mac Pro? Connect three monitors. Know how to get your 3-monitor rig to work with 3 monitors? Downgrade to Mountain Lion. Which - yeah. It's an 8-year-old computer. but it's an 8-year-old computer that's faster than the new Mac Pros.
I have only cursory experiences with the Surfaces. A friend of mine was convinced that it could replace and exceed his laptop's functionalities. He used it to put stuff on the TV while we were at his place with about as much grace and trouble as you had with your screens. I tried navigating the awful Metro UI that somehow thinks swiping in from the edge of the screen is a logical thing. All I learned from that experience was that I will not touch a Surface with a ten foot pole - let alone a freakin' stylus. My approach to technology is always that I want the best tool for the job. I don't really care about one manufacturer over the other as long as I get what I want out of it. Which is why in the last years I went for a desktop PC but a portable MBP Retina; an iPad tablet but an Android phone. There's benefits to staying within one ecosystem but the advantages of being platform-independent outweigh that for me.
So far so good with Windows 10 indeed. Had my outdated GPU driver that caused some problems but that's about it. I do know people whose devices got ruined because of installing Win10, but the common denominator is always that it was a crappy / old device in the first place.