Typically, this can indeed be a headache, and is indeed why larger organizations typically use vastly outdated products and services. Since you are starting from scratch, however, I would recommend researching any issues you might have as you go, while you attempt to use the latest version possible. Chances are, you are not alone in your woes, and possibly there's a solution online.

In your case, it looks like you need to add in something like: https://docs.djangoproject.com/en/1.10/ref/settings/#allowed-hosts, where you give the possible allowed hosts that can actually serve your site.