Works for me with OSX and DO.
Did that two months ago. Took about 2 days of tweaking and 3-4 days of getting SSL.
My resources:
Base on:
I actually use all of those resources and wrote my own tutorial in Quiver (osx app for code snippets and documentation).
I can create blog post on how to do it if you like? I need to clean out the secret keys and passwords relating to my production server though from the quiver note. I am also in the middle of doing my thesis and graduating. But if you give me about a week I can have it in blog post. My setup skipped Nginx.