beeware
Just make it super-easy to install
Ignoring completely how to pay the piper, I do have an opinion on how to make something successful. Perhaps you could sell the install process. The software is open source, but a locked-down, pre-install VM with a web admin interface costs money. I can tell you right now, if I could pay for various systems which would just boot up as a VM, let me set the machine name and hook up my own authentication, that would make things so, so much easier. I'll pay a per-VM license fee for commercially supported applications which do things like version control, continuous integration, application support, running corporate applications etc. If I could just give a VM straight to the relevant team that they could boot up and configure in 15 minutes, with decent logging and a basic support arrangement, that would be amazing.
And I could evaluate such things myself internally by installing the open source code into a Linux VM that I'm maintaining on my laptop, or go to the effort of running my own if I need to.
In my experience, if the cost of application maintenance can be made low enough, that will be preferred to paying for an internal developer to support it. Companies are often looking for ways to capitalise their expenditure to reduce their operating budgets.
If you've got a SaaS - sure, this would work. However, what if your project isn't an application, but a library (e.g., Django). It's already super-easy to install - that's what PyPI is for.
I agree it's an interesting idea though - the sort of thing that Docker (or, at least, the concept of Docker - not passing judgement on the specific implementation) makes possible, as long as there's a way to put a paywall around a Docker image.
If you've got a SaaS - sure, this would work. However, what if your project isn't an application, but a library (e.g., Django). It's already super-easy to install - that's what PyPI is for.
Django is super-easy to install, but it's hard to deploy. What about a VM or docker images from a private registry that power your site?
I've done a lot with docker and Django at cookiecutter-django. We are at a point where a user can deploy his project with a couple of commands. It's basically just apt installing docker, cloning the repo und running one docker command to power up the stack. This works because the whole project layout and the settings are already set up by cookiecutter.
For vanilla Django Pro to make it super-easy on the deployment side, all a user would have to do is set something like DJANGO_PRO_DEPLOYMENT=True (this is obviously a bad name, but you get the idea) in settings.py and all the configurations for DB, CACHE etc. are filled in automatically.
Tools like docker-machine make it extremely easy to set up remote machines on basically every hosting provider, so you got that covered. Private registries can be bought directly from docker and there are SaaS companies out there that manage your subscriptions for a fee.
Leaving us with the code that has to be written and maintained :)
Spinning this a little further: Once something like this is in place, this is a gold mine for ongoing support contracts. If the Django project itself has no interest in offering support directly, it could reach out to contractors that are interested and pushing clients to them. A contractor might pay a monthly fee for this service, or pay a provision for every new client.
