Hi shorty. I live lin Sydney, the northern Beaches to be exact.
Commuting cyclists are a bit of a minority on my local roads, but that hasn't stopped me from getting on my bike and being part of the traffic.
Sydney has good riding conditions - in the winter it's not that cold, and it doesn't rain very much.
But then you have to take into consideration the hills around here and the not always bike-friendly traffic. Oh well, no-one ever said life was perfect.
The idea of a cyclo-cross bike is a good idea. The condition of the roads around here aren't always that good, and there are shared pathways/ bikepaths where wider tyres might come in handy. I've been commuting on a hybrid and have considered upgrading to a touring/cyclocross bike myself.
If you're interested in riding away from traffic, we have a few national parks around here - Ku-ringai Chase & the Royal National Park. My fav national park ride is around Church Point and Akuna Bay (a good chance to pratise climbing hills)
The state Bicycle organisation is Bicycle NSW
http://www.bicyclensw.org.au/
Some local bike User Groups (BUGS) and rides, can be found here http://www.pushon.com.au/
Bikely is a good site to go to check out any possible commutes:
http://www.bikely.com/
Here's the RTA's official bikemaps
http://www.rta.nsw.gov.au/trafficinf...sydne_dl2.html
A good mass group ride is the "Sydney to the Gong" ride - It's a 90Km bike ride which goes down the coast to Wollongong.
http://www.gongride.org.au/
I hope this is of any help,
Happy riding
I've put up a picture of my fav place to ride - North Head