I've been 90% leaning to the SYD loop, so the advice so far helps to confirm that I will have plenty to see in the region. The Unyoked thing looks interesting, but is booked for my dates. Not sure I want to go that far off grid - I do like to be walking distance to a pub.
I am at the Holiday Inn Old Sydney for the first night. I arrive at 5 AM so figure that is my best hope for an early check in since I am IHG Platinum. It is also a Chase anniversary night that is now expired, so I can't change it. I'll just take the train from the airport.
As for rental car logistics, would I be better off taking the train out of downtown to a local office? Looks like Avis in Wollongong is $25/day less than the Circular Quay location near my hotel and only a 10 minute walk from the North Wollongong station. I'm not overly concerned about the price, but if it saves me hours stuck in Sydney traffic it is worth it. I also see a Hertz in Katoomba but don't see any availability. Any other spots to consider for a pickup other than downtown and the airport? Thanks.