Interesting a trip many of us have done and took it for granted Newcastle to Pittwater, I sure wouldn't like to be out there in that wind from any other direction.
The trip into Pittwater at night and being so tired into a westerly gale would be terrible.

Reef down and go! Best to stay inshore as Ramona says.
In 2014 we took the Sailors with Disabilities Lyons 54 'Kayle' to Southport. 48 hours dead CYCA to the SYC. We had 50 kt gusts and were doing 15-20 kts at times, with just a heady. It wasn't what I would call a pleasant passage, freezing water half a metre deep rushing over the decks every few minutes, but it was exhilarating.
We went from headland to headland most of the way.