I think Apple updates have really slowed down. I loved the Apple that had yearly updates of all the Macs (boy, that was a long time ago). Apple of today always put themselves in a corner when it comes to processors they want to use, and Intel not delivering them in time. I would preferably have Apple just put out more incremental updates instead of waiting years for larger updates.
Yeah, I agree the MacBook was nice. They only had to add a second USB C port. But you see where the tech is going: the iPad Pro. The MacBook had all the crappy stuff, as you noted, and the iPad Pro got all the good stuff (camera, speakers, mics, face ID).
It would be nice if Apple were to introduce an ARM based Mac, but Apple is so slow in moving things on the Mac (years and years for a new Mac Mini, Mac Pro, and the MacBook Air) that I have no confidence it will see the light of day in 2020 (because they have to introduce the OS to developers first, so it means it will take up until 2021 for such a MacBook to come to market). I could be wrong. It is likely, though, Apple will move to ARM.
Microsoft is at least doing some new things at a more steady pace. Yeah, before the introduction of the Surface, I didn't like Microsoft that much. Although Surface RT was a bit wonky. But they have shown that with better leadership they can come up with new stuff and actually bring them to market (previously it was always concepts and demos, a.k.a. vaporware). Surface Pro X seems nice. If you can handle Windows, why not? So perhaps wait for WWDC 2020, and if nothing new comes up, go for the Surface.