Missing items from menu

Could you provide a link to your site running Dusk to Dawn so I can take a look at the menu?

Could you provide a screenshot of your menu setup in the admin area?

http://en.support.wordpress.com/make-a-screenshot/

You can upload the screenshot – in a graphic format like JPG, PNG, or PDF – in your Media Library, and provide a link so I can see it, or upload it with a service like Imgur or Snaggy.

You should be able to have more than five top-level menu items, as you can see on the demo here:

https://dusktodawndemo.wordpress.com/

Have you made any modifications to the theme files at all?

Thanks for the screenshots. I can’t tell if you’ve assigned your custom menu to the theme or not, because the menu assignment checkbox isn’t included.

In order to assign a custom menu to your theme, you need to assign it to the theme. Could you verify that the “Sidebar Menu” checkbox is selected below your custom menu? It should look like this:

I’m not sure why you’d be missing the menu-assignment checkbox, but you can also create custom menus in the Customizer, so you could check there too:

Perhaps there’s a conflicting plugin. Try temporarily deactivating (not uninstalling) all your plugins. Do you see the checkbox? If so, turn the plugins back on one-by-one to find the conflict.