I don't know of OS X breaking updates as acute and widespread as Windows, but the space of Apple machines to test is small and predictable, where Microsoft faces an essentially impossible testing task.

Beyond that, though, Apple laptops seem to just have shitty wifi connectivity. At a guess, it's one of the downsides of metal unibody design (along with godawful native speakers), but it seems almost universal. Things have improved, but strength, speed, and range never seem competitive with non-Apple machines at a similar price point (or half that price point).

I haven't had connectivity issues, other than it takes a while to switch networks... At home, my macbook has about the best connections of any of my hardware, though my Nexus 6P may be better. I've been able to reliably copy files at 200Mbps+ over wifi. Worth noting I've got fewer than a dozen devices on wifi, and neighboring signals aren't that bad where I live.

At work, it's a bit noisier.