Nice original post.
I started back on a sinclair ZX-80, in 1980, then upgraded to the ZX-81, VIC20 (colour machine on an old b&w TV!), C64, various Amigas before going over to PC in 1994. Then from 2005 until last year it's been Apple all the way. Running Bootcamp, I considered my Macbook Pro & iMac 5K to be the best Windows machines ever built - until the Surface Book came along.
Horrendous bugs have been creeping into OS X over the last few years which have had a real impact (like remote disks not mounting in early Yosemite, or dodgy Bluetooth dropping the mouse in El Capitan, which didn't happen when bootcamped into Windows) so I opted for a Surface Book as my main machine, having had a good experience with the SPro3. I like OS X a lot but if it's going to get quirky and take Apple a long time to fix howlers, I decided I'm better off in Windows full-time. I couldn't be happier despite the SB's flaws, and with Apple clearly not expecting anyone to use the new Macbook Pros in my sort of environment, glad I took the Microsoft option.
My home machines will continue to be Macs until they bite the dust, & they've always had exceptionally long life. When they need replacing I'll survey the landscape, but the Surface Studio looks tempting already!