Same issue. This is frustrating, as I see no official statements from Apple this is not supported. The iPhone and Watch simulators are paired, but no iCloud on Watch. I tried everything, and I guess I have to start using physical devices. Very disappointing.

Has anything changed, or is CloudKit still being blocked on watchOS simulators at this point? (I'm new to iOS/watchOS development but the lack of clarity and plethora of bugs has not been a nice experience coming from Dart/Flutter environment.)

Good to know I am not alone.... ! Exactly the same issue here. Checking their system status they say everything is cool: https://www.apple.com/support/systemstatus/ But. App Store connect login does not work at all.

Sure it works, but why not having a simple context menu just like VSCode in Dart/Flutter: right click -> refactor -> remove this widget. In their world, a widget is a view. At high level, the same thing. I guess they try to make things truly easy and friendly. On the other hand, Xcode depends on workarounds. They usually work. But painfully (in comparison). User-friendliness seems not be a priority for the team.