G'day Crazy,
The only time I have sailed the Tasman ( Bass Strait to Cook Strait) was in late January.
However..... in the day job I spent about 18 years on Bass Strait ( about 3300 crossings more or less ) plus 3 years before that running across the Bight to the west and also a couple of years on rig boats in the Paddock. Also about 20 years
small boat sailing in the area in all seasons.
Winters can give very settled
weather, depends on the year. Gales are usually quite honest... you see them coming and.. well.... they are just gales.
Worst time is typically August/Sept with April not quite so bad...the equinoctial gales.
Late spring/Early summer gives storms... not many but can be bad... short sharp and nasty... from October into very early January.
So nothing intrinsically wrong with a winter crossing ( depends a lot of course on
boat and crew).
Problem is picking if it is going to be a hard season or not, dry year ashore...good winter
weather and v/v.
Dunno if I would be wanting to make a landfall on the
west coast of the South Island in winter..... maybe I'm just getting soft.