Hort said..
First LH trip I did was many years ago during March , two handed in an old Holland 30 half tonner. Great trip out, on the way back we had 3 days with the kite up, then got smacked by a southerly. We were aiming for Port Hacking , ended up pointing at Newcastle & in the end made Broken Bay. The problem with these sort of passages in small boats is you can't sail fast enough to stay in the favourable weather window. You need to be flexible and prepared to tough out some heavy weather. Subsequent passages were in the Gosford LH race in much faster boats. Even then we always seamed to either get smacked on the way there or coming home.
Also the lagoon can be twice as windy as at sea. We got caught one year & couldn't get out to our boat to get underway. It was blowing 50kn across the lagoon but only 25kn at sea.
In 2016 DrRog and I both got seasick in the lagoon getting on the boat to depart for home. As MB headed out of Erscotts we had really horrendous conditions (watch DrRog's video of the trip), we shouldn't have tried to get out but we did, and got hammered for a long time.
In 2015 Havefun, Cisco and I were stuck onboard for 24 hours in the lagoon because of the wind. Cisco and I had a few beers, watched the cloud formations on the mountains and read a book or two. Havefun doesn't imbibe, I'm not sure what he did.
Yep, the lagoon can be nasty. It would be absolutely horrible in the strong westerlies in winter and I am sure that you would have to leave the lagoon and either stay at sea or maybe anchor open ocean on the other side of the island in over 10 metres of water.
And then you would have to come home against that wind.
I have been allocated the best mooring this year (North Passage 3) for the November rally. I am still after crew with offshore experience if anybody is interested. PM me.