Porting from django 1.8/python 2.7 to django 2.2/python >= 3.7

This topic is just the conversation I am looking for!
I’ve come into a large project stuck at Django 1.5. The goal is to move this 10 year old project to python3 and a current version of Django 3.x. There is also a desire to do a code audit and dump cruft.

  1. I’m wondering if it would make sense to copy/port code into a fresh install of Django 1.11 then do Python 2.7 -> 3.7 and finally follow the minor version upgrades to the target version? similar to what adamchainz suggested.
  2. Or copy/port django code to Django 3.0 and also change python from 2 to 3 at the same time?

My gut is saying option 1. which is more inline with admanchainz suggestion, but my gut has been known to get things wrong :smiley:
Any discussion on this topic would be a huge help, Thank you in advance!
-Trey