There are a few Aussies on Sailnet, One of them is a marsupial of dubious hippy persuasions that one should be a little wary of
Now I would hate to give other boards a plug but if you also try cruisers forum there is a large Aussie sailing contingent there.
Best of luck to you......it sounds like you have some understanding of navigation and the sea, with just the sailing to master. Like I said anything we can do to help please let us know. Heading north from down here it's best practice to wait for a southerly change and once the strength of the southerly is determined and it has subdued to a reasonable level depart for your next northerly port on the back of it and keep going until the north easterlies typical of this time of year begin again...then once again it is a waiting game for the southerly...with mild north easterlies and minimal swell one can also make some ground north motoring where possible.
Meanwhile enjoy Broken Bay. It is my local cruising ground, and although busy this time of year there are some nice little spots, although of course no comparison to your part of the world!
The mouth of Broken Bay past Lion Island is basically ocean conditions. Might be worth your while sailing around out there in different conditions and getting a feel for the boat. On the north side, in the Bouddi National Park is Maitland Bay, it is a beautiful beach that would require you to cross the mouth of Broken Bay to access it and might also make a good little test sail, with the promise of a pretty little anchorage at the end.
Also of some use to you might be the following east coast passage planning tool.
Passage Planner : Skipr.net