Gday Brian,
Welcome to the TH site, & congrats on TopKnot.
As you know the NSW coastline is not to be taken lightly.
I was once strongly talked out of a whimsical single-handed jaunt from sydney to lake macquarie, im very grateful that they did, i then learnt to prepare properly(albeit with many mistakes along the way).
The Alan Lucas book is a must have.
check the NSW Maritime regulations for coastal , as you can bet there will be some differences to the regs you are familar with in QLD.
In my opinion you will have to do a few overnighters, by pulling into every suitable port, it will make the trip many times longer, not only that...could be safer staying out to sea rather than negotiating an unfamiliar Bar entrance on anything other than a perfect tide & conditions. As a general rule the bars get worse as you go Nth.
Your plan of not sailing to a set timeframe schedule is a good idea.
I have the paper charts if you'd like to borrow them.
Research a few ports along the way, if you have to break the trip & leave the boat somewhere. A commercial swing mooring at Laurieton/Dunbogan is about $195 a month
a bit pricey but its a nice place here. And stop in if you dont mind a few enthusiastic TH owners crawling over TopKnot
.
Shoal Bay at Pt Stephans is a fantastic spot to stop, plenty of free visitor moorings, but no fuel was available
, you can sail or catch the bus to Nelson Bay for fuel.
There was a detailed discussion over on the compass owners website, about installing that autopilot.
My st2000 only struggles on the TH when im over-canvassed.
Marinka recently did the trip, & theres a write-up about it in the Voyages section. I'll look forward to reading any updates about your prep for the trip.
cheers
shaun