Django (and DRF if you use it), uses too much reflection, which doesn't play nice with type annotations. The strategy that works for me is to annotate my application code, and keep using dynamic typing when interacting with the framework.
When I tried them a year ago, they used "Any" a lot, especially around the ORM code (Django) and the serializers (DRF). Since those are also the parts where type checking would be the most interesting, I didn't find a lot of value in using them.