Service NSW says;
The sign indicates that you are able to park for a maximum of 2 hours between 8am and 6pm and a maximum of 4 hours between 6pm and 10pm. Between 8am and 6pm you require a ticket however it is free. Between 6pm and 10pm you require a paid ticket if you are parking for more than 30mins.
From looking at the sign provided it appears you would have 10mins + 4 hours of parking time as per your example.
For further confirmation it would be suggested that you contact the Police or the local council parking rangers as they are the authorities who would be enforcing the parking in the area.
Inner West Council says;
As it stands currently, the parking meter accepts payments from 5:30pm, should you arrive at the carpark after 5:30pm you are able purchase a ticket (to cover the paid period of 6pm-10pm).
If you arrive prior to 5:30pm, a free ticket must be displayed and you would need to return at 6pm to purchase a ticket.
The frustrating part is I believe there is still an issue with the crossover time period;
The sign implies that you can park there for at least two hours at any time, but from your above description, if you park there between 4:01pm - 5:29pm the maximum time you can park would be 1:59min - 0:31min, which is less than 2hrs.
Of course 1:59min is not unreasonable, and waiting a minute or two for the time to tick over to 5:30pm also not unreasonable (assuming you knew the ticket machine changed its rules at 5:30pm),
but anyone parking there at ~5pm is only going to have 1hr of parking, which seems contrary to the signage.
Is there any reason the ticket machine can't cater for crossover times greater than 30min ?
Unfortunately my time has run out and I haven't been able to nail down exact rules and definitions sufficiently to warrant to time and cost to take this $100 issue to court.
