Heck, Apple has become the "conservative" choice for a computer that is boring but will work with fewer problems. How we got here I have no idea.
See, I've had the exact opposite experience with my Surface. Most of the people I know much prefer MacBooks but are exploring the possibility of switching to something in the surface line. I know some of my friends had initial issues with the Surface Book but now they love it after much needed updates.
I think sometimes Microsoft pushes hardware out a little too early but, at least in my experience, they always make it a great experience even if it comes after several updates. But like Apple products it's usually best to wait until after the initial kinks work themselves out anyway.
MBPs are still the best computer one can get for a rock solid Windows experience; even the surface book trackpad (supposedly precision?) seems to not really compare to what comes on a MBP, and touch doesn't often fill in the gap. Over the last years, I've always regretted my PC purchases (4), but have never regretted my MBP purchases (3). It is really hard to come up with the courage to try again.
https://medium.com/@searls/warm-takes-on-microsofts-surface-...
Going back to my rMBP for work feels limiting and slow.
There are workflow changes and difference I'm having to work through. They are different systems, after all. But it's been a good experience so far.
I currently own a Surface Pro 4. I love it. I had some issues up front and Windows is still Windows but it's gotten better and so far I love it. I'll admit it's impossible to beat a MBP's trackpad.
But as with everything I've seen folks with basically every opinion on the Surface line. So your mileage may vary.
The SP4 I have is better but still has issues with sleep/hibernation, at least compared to every Mac I have used. With my Macs I can leave them for a week and they will wake up immediately, and still have decent charge. I leave the SP4 for two days and it is dead. Leave it for a few hours and it takes 10 seconds to wake.