Why a module's singleton method is not visible in downstream eigenclasses where it gets mixed?

First of all, include does not include eigenclass methods as you might expect. Consider:

module Foo
  class << self
    def do_something
      puts "Foo's eigenclass method does something"
    end
  end
end

module Bar
  include Foo
end

puts Bar.do_something
# undefined method `do_something' for Bar:Module (NoMethodError)

Note that this is consistent with the behavior of classically defined class methods:

module Foo
  def self.do_something
    puts "Foo's class method does something"
  end
end

module Bar
  include Foo
end

puts Bar.do_something
# undefined method `do_something' for Bar:Module (NoMethodError)

A common idiom is to define the class methods in a submodule and then trigger a call to extend when the module is included:

module Foo
  def self.included(base)
    base.extend ClassMethods
  end

  module ClassMethods
    def do_something
      puts "Foo::ClassMethod's instance method does something"
    end
  end
end

module Bar
  include Foo
end

puts Bar.do_something
# Foo::ClassMethod's instance method does something

The second thing to note is, that you are really including the instance methods of Automobile into the eigenclass of Vehicle, thus the instance methods of Automobile turn into (eigen)class methods of Vehicle.

Your Car class basically has nothing to do with all this. The only thing to note here is, that class inheritance also makes class methods available, whereas include does not. Example:

class Foo
  def self.do_something
    puts "Foo's class method does something"
  end
end

class Bar < Foo
end

puts Bar.do_something
# "Foo's class method does something"

First of all, a class is an object, just like the other objects it also has its own superclass; second of all, Eigenclass itself is a normal class, only anonymous and sorta invisible; third, the eigenclass's superclass of the derived class is the eigenclass of the base class; Fourth, include includes instance methods (not singleton methods) of the included module, make them instance methods of the receiver class object.

There're two parallel inheritance chains in your example

Car < Vehicle < ...

Car's eigenclass < Vehicle's eigenclass < Automobile < ...

Do the following test on irb:

class Object
  def eigenclass
    class << self
      self
    end
  end
end

Car.ancestors # => [Car, Vehicle, Object, Kernel, BasicObject]
Car.eigenclass.ancestors # => [Automobile, Class, Module, Object, Kernel, BasicObject]
Vehicle.eigenclass.ancestors # => [Automobile, Class, Module, Object, Kernel, BasicObject]
Car.eigenclass.superclass.equal? Vehicle.eigenclass # => true

You see, Automobile is in the eigenclass inheritance chain. But regretably, the ancestor method doesn't return invisible eigenclasses, nonetheless they are actually in the second chain.