3. We teach types to students as young as 12. They have no trouble with the concept, because they're taught from a young age about classifying things, and types are a form of classification. So there's nothing "unintuitive" about it. The people who have the most trouble with types are adult programmers who were raised on languages with awful type systems, like Pascal, and cannot envision any other kind.
Furthermore, we use types as a central notion in our program design curriculum. The structure of the data (aka, "types") provide a hint as to the structure of the program. This helps students who are stuck get unstuck. That is, they are most helpful to the students least able to get started, which seems like quite a valuable place to focus.
Of course, having annotations and enforcing them statically are two different things. That's why Pyret lets you check annotations dynamically instead. And that makes it even simpler and more intuitive to introduce the concept.
2. Direct integration into the syntax of the language makes a huge difference. There's no library and additional complexity. For rank beginners, every new "moving part" is a source of problems. This is why most Python curricula do not emphasize writing tests early. In our curricula, students begin with writing examples of their program's behavior — expressed as tests — and use that to help figure out the way the program must work. (Just like you use examples to help figure out a more general structure in other disciplines.)
4. Event loops are central to reactive programming, i.e., animations and games. HtDP 2nd edition begins with writing an animation. The Bootstrap curriculum is focused around teaching students to write a game — but in the process learn algebra. It's niche to you because you have a particular model of programming education, which may well resemble what people were teaching in the 80s. That doesn't mean curricula haven't moved on. And we're talking about education, not production, which are two different things.
5. Combine the earlier points for this one.
Whenever making "I haven't seen", "I don't see", etc. comments, it may be helpful to keep in mind Paul Graham's Blub Paradox [http://www.paulgraham.com/avg.html].