I think if Aus $$$ is worth more than american money you paid WAY too much for an 11yo bike.
Hell if you walk into a Honda Dealer here in the U.S. with $5000 cash you could probably walk out the door with a brand new 2007 VT750. Or 1 that is less than a year old and basically brandnew still under warranty.
Aussie dollars are worth less than US dollars (but catching up fast!) and you'd obviously be surprised what used shadows go for outside of this country. Your scenario is useless - he's not in the US - it's simply not applicable.