I like the idea of this. I've known about and briefly used Django since 2007, but I really ramped up use in 2017 building a bunch of MVPs (that apparently are still in use) for startups.
The majority of my challenges with it were in managing authorization (in DRF) and initially breaking away from Jinja and using a frontend framework instead. The documentation was generally easy to follow, but I did get a habit of going through the source code, because it quickly turned out documentation was terse. If I remember correctly, that was primarily when I was trying to handle auth and trying to understand the ORM. I think I also had to learn how to create Django commands from example, but that's something that surprisingly was very helpful.
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