There are usually several quite experienced ocean cruising club
members doing that passage
. Nina Kiff was the club organizer in NZ.
I will offer some caution about the "safety in numbers" concept
. My personal observation is that groups of sailors often make worse decisions (about weather
windows) than the individuals would. In part this is because what is a good window for one boat and skipper
is not necessarily good for another, but there are also simply some odd group dynamics. And once at sea, you are pretty much on your own.
None of that is to minimize the value of talking and sharing with other experienced cruisers. That 'community" is one of the joys of the cruising life. But realize you must be absolutely self-reliant and strong enough to make the best decisions for your own individual situation and not 'follow the herd".