babayega2

I am currently doing the opposite. Moving an old Java stack to Python/Django. Been able to do so under 9 months. I think upgrading to Python 3 should be doable. What's the version of your Django stack? You just need to try to reach Django 2.2. And if you are at Django 1.1, 90% of your code can be upgraded to Python 3. Nothing fancy. You just need to use libraries such as pyupgrade [0] to automatically upgrade your code, combined with black [1], flake [2],... Everything is done in less than 20 commits. From there you jump to 2.2 which supports Python 3.6+ .

It will be very difficult to implement all the goodies given by Django ORM/SQLAlchemy. But ... You if Java/C# is the tech that you feel confortable with, no problem. You have to use it. But, I really think it's easier to understand the "business domain" of Python code than Java/C#.