My medium-sized Django projects had close to 100 dependencies, and when you want to update to a new Django version, the majority of them must be updated too.

Thankfully, updating to a new Django version is usually simple. It does not require many code changes.

But finding small bugs after an update is hard, unless you have very good test coverage. New versions of middleware/Django plugins often behave slightly differently, and it's hard to keep track of all the changes when you have so many dependencies.