Yeah, in Sydney, do the harbour cruise or at least jump on one of the ferries.
You Aussies need to help him out more on the "off the beaten path and hang with the locals", I reckon. More recently when I've been to Sydney I've been hanging around in some of the inner city suburbs and its been great (Paddington, Surrey Hills, inner west).
And I can't believe there has been no "Melbourne is better" spam yet either