I feel your pain. If maintainability is your concern, I would advice to skip this release as it won't have long term support. The current LTS release is still 2

I feel your pain. If maintainability is your concern, I would advice to skip this release as it won't have long term support. The current LTS release is still 2.2 and will only be replaced with 3.2 sometime in 2021. You probably already know, but the long term release timeline is shown at https://www.djangoproject.com/download/ https://www.djangoproject.com/download/ Sticking with LTS releases really helps. You'll still have nearly a year to migrate from one LTS release to the next. In my experience it also helps to avoid small (e.g. a single developer) and young Django apps and stick to the big ones. The amount and quality of the documentation can also be an indicator of longterm viability of the project. I've done a few more significant migrations (including Python 2 to 3), and about the only bad things are apps whose development stopped and those with developers implementing hacks using Djangos internal API. Everything else is usually done in less than a day for the whole Django project. I only did small projects with 5-10k loc, though.