I occasionally write them as a form of documentation - when it would be more concise than explaining in prose.
There is nothing specifically 2.x-style about making use of dynamic typing - it's a core property of the language. While 3.0 introduced the annotation feature, it wasn't even specifically intended for typing (https://peps.python.org/pep-3107/) and standard library support wasn't added until 3.5 (https://docs.python.org/3/library/typing.html).
>As the second group continue to add increasingly complex typing features to the language, I wonder if Python is becoming less desirable for those in the first group.
Some new changes have been missteps, in my view. There's still nobody forcing my hand when it comes to typing, really; I just shake my head when I see people trying to make it do things it really wasn't designed for. On the other hand, there are definitely things I'd love to see improved about the language.