Does anyone else feel like maybe the entire iOS development experience is batshit insane?
On the other hand, you do get greater performance and stability (but not perfect stability, after all it wouldn't be an iOS release if Apple didn't break something and completely ignore radars).
That said figuring out bugs in iOS is a major league PITA. I have one now in NSURLSession which is batshit insane.
And autolayout is freakin awesome imo, though I hear a lot of people groak about it.
Something else I really dislike when it comes to constraints - they don't play well with animations, at least in my experience. I recently created a view that had a variable number of square buttons in it that were laid out in a grid two rows high. Making a nice animation when you add a new button, fading in the new button, and sliding the others out of the way was nigh on impossible (ie 'not possible without writing more code than if I had just done the layout manually). And yet, this seems to be the perfect use case for auto layouts...
I often wish we had something akin to autolayout for CSS.
But for my big projects I do 100% of the UI in the code, if the UI use a lot of custom control, it just not worth it to use IB, the end result is that what you see is not at all what you get. BUT it improved a lot with Xcode 6, because now it can render custom views live in Interface Builder.
Auto layout on the other side.... it's just broken.... Every time I try to use it I got what you mentioned in your first paragraph. And I do a lot of animations in my apps, and playing with 10 constrains instead of a simple frame is just .... too much of a burden.
Again, for big custom apps I don't use it, but I love those functionalities for small & simple apps.
Plus the term "batshit insane" has been overused. What you'd use to call some really bizarro thing when you do see one?
Even with a problem like this, you can fix it or get around it with a bit of trial and error. As with any other black box technology.
(Still useful to know, though.)