Perhaps there is a definitive tutorial or blog describing what I'm looking for, but I haven't seen it. And being new to Django, I'm really looking for a proper way to both set up a VPS and deploy the project to it ... the latter in a repeatable/sensible way as the project evolves.
Here is what my project looks like:
I would say Test-Driven Web Development with Python is a good one. It's mostly focused on TDD, but it's really good at covering the basics of Django as well. Chapter 8 talks about deployment and is pretty thorough.
EDIT:
Saw that that book doesn't use S3 for static files, so I'd recommend this blog post for dealing with that.