Instead, we should permit any expression to be used. If a value does not expose an __enter__ method, it should behave as though its __enter__ method is return self; if it does not have an __exit__ method, it should behave as though that method is return False.
I'm not sure why you would want this. But it is really easy to implement with a named function already. I think it would be better to experiment with a wrapper function first, maybe put it on PyPI, before changing the language for something whose purpose is unclear (to me).
I think you probably mean something other than what you actually write. It doesn't really make sense for "any expression" as far as I can tell. What would it possibly mean to write:
with (2+2) as foo:
print(foo)
But anyway, my toy simple implementation which satisfies the stated requirement: