The constant nagging for updates could be considered a flaw in design. I think Microsoft has always had the reputation of producing buggy software with usability issues. I think they have gotten a lot better at all that.
Definitely stuff like NSA-level telemetry and aggressive updates are bothersome. I was talking more from a programming perspective. They seem to put out comparatively bug-free and performant software. Specially on android, I was surprised to observe that Microsoft's apps are generally better designed and more useful than Google's own stuff.
