Through the use of the Poetry project, incremental changes, and a little luck, the Django 1.11 -> 2.2 and django CMS 3.4 -> 3.7 upgrade was a success, but not without some excessively harsh profanity.

The Django shell provides an environment where developers can interact with the database via Django's ORM. While the shell is great for basic interactions, it quickly becomes laborious to work in, be it due to manual imports, having to scroll through shell history to repeat commands, or working with / viewing queries returning more than, say, 20 records. These issues, and more, can be remedied by interacting with the ORM in Jupyter notebooks, using Pandas.