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Late autumn, winter and early spring (April to September) are definitely the best times to climb in the Sydney region. The temperature almost never drops below zero degrees Celsius in the Sydney basin, and the weather is usually pretty stable during this time. It can get pretty bitter at shady crags that catch the wind (eg. Bangor West), but generally it's always possible to climb during the cooler months. Friction on the sandstone is also at its best when it's cold.
 
Climbing in summer is a real battle against the grease. It tends to be unbearably hot (35+ degrees Celsius is pretty common) and wet as well, with stinking hot humid days followed by seemingly endless days of torrential downpour that are barely any cooler. The shady south and east facing crags are the pick during the hot months, with Narrabeen Slabs and the Cathedral being good options. The sea cliffs are also a good option, since they are usually in shade by mid afternoon and swimming is usually possible. The boulders on Palm Beach are probably the pick of these areas.
 
Another disincentive for climbing during summer is the sea slime, which coats most of the sea cliffs and crags near the ocean. This can also happen at other times of the year, particularly if the prevailing weather is easterly.
 
Good sun protection (sunscreen, hats etc.) is an absolute must during summer. Foreign visitors should be particularly careful not to underestimate the power of the sun.
 
The sandstone found in Sydney is quite porous, meaning that many of the crags seep during and particularly after rain. The rock also has a tendency to soften somewhat when wet, so take care if you're cranking on small holds after rain.
 
The Australian Bureau of Meteorology website (at http://www.bom.gov.au/) is an excellent source of detailed information on Sydney's climate. Amongst other things they provide an up to date Sydney weather forecast and an almost-realtime Sydney Rain Radar.
 
The following two graphs give a bit of an idea of Sydney's climate throughout the year (courtesy also of the Bureau).