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Some years ago I scoured the area south and west of Sydney using a C8 as a test scope for seeing etc.
Sites below the escarpment is pretty much useless for stargazing, there is often an inversion layer over the coastal strip trapping a lot of moisture near ground level and worse, at night there is a lot of salt carried from the breaking surf and this reaches a long way... no good for telescopes. The sky might look dark, but mostly the transparency is poor and seeing terrible.
The first decent site I found was the carpark at the "Barren Ground" park, it's not very dark though.
I've stayed in weekenders in the hills above Berry, Jamberoo and Kangaroo Valley, as long as you get well out of the valley these inland places are OK.
Then there's the hill above Kiama, at night the gate is locked but if you're OK with staying the night its not bad.
Inland... try the roads around Robertson, there are quite a few quiet spots you can use. However, going further west means approaching Bowral/Mittagong... the southern highlands are the cloudiest part of Australia and pretty much a waste of time.
There is also the road from Wollongong that joins the Hume (M32) somewhere near Sutton Forest/Goulburn, there are useable places on that though in winter it can be very very cold there (and will snow).
Lastly the main problem i found down south is dew - the farming areas in most of this region have dark moist soils. The only way to avoid this is to head for a sandstone area which is not farmed.
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