The short version:
release message when a Cocoa application terminates?
It's not just views. It's everything. I don't think even the NSApplication object releases itself.
In fact, I'm pretty sure (but not 100% certain) that the answer to my question #1 is: "Because releasing subviews is unnecessary when the application is about to terminate."
I believe so as well.
If you want to your custom object graph released at quit, have your app delegate own it, and release your other top-level objects in applicationWillTerminate:. As long as you're managing all your ownerships correctly and you release every single top-level custom object from that method, all your custom objects, including views, will die.
Note: I have not tried mixing this with Core Data. It may or may not be possible to do this to your managed objects. I don't have any first-hand experience with that.