> remember most Python devs have little experience with staticly typed langauges, so in practice your team will be skipping annotations - e.g using Dict[str, Any], which defeats the whole purpose of annotations

Using mypy or pylance gives benefits even without annotations, and while you can often do better than Dict[str, Any], rough cut annotations like that often, IME, provide value. (For one, they’ll catch paths that would allow either the dict or a key in it to be None when that isn't expected.)