John Moulden: If you are in correspondence with Hugh Anderson you certainly have a good contact for the Australian folklore side. Being based in Victoria, he has not quite the direct access to convict records that he would have in Sydney, but these things are all out on micrifilm (and probably database) nowadays.
Anyway, you say you are now looking beyond the records and considering newspapers. There are only the two widespread daily papers in Sydney: Fairfax Press' The Sydney Morning Herald and News Ltd's The Telegraph/Mirror (or whatever the combination of their erstwhile morning and evening papers is currently called.
The SMH is a morning broadsheet with a more serious tone while the Tele/Mirror (aka The Terror) is a tabloid with a stronger emphasis on sport and TV. I don't know which would be likely to run a query ... and which would bring results. Interestingly, it is the Tele/Mirror that runs a permanent history page and has done so for decades.
Two of my younger brothers worked for News Ltd as photographers in past years and a sister-in-law has been a journalist for both. I can sound out her suggestions on the best way to follow up these family links.
If I can get the blue clicky things right, this is a link to the SMH home page: