One has to ask does this meet APF regulations in hopping over a built up area?
Provided the target area (DZ) meets certain characteristics there is no issue. Jumps into populous areas are classed as "displays" and have to meet stricter guidelines than the usual jumps in rural areas. If you have a concern, you could contact the state Safety Officer whose details you will find on the APF website.
Responsibility for safety of the drop largely rests with the meat bomber. If as you say there is a possibility of a number of frequencies in use then the workload on that final jump run will be a little high.
We used to see jumping into the ocean between Fremantle and Rottnest a few years back without too much problem. Perth Radar were always good at keeping the jump aircraft and those transiting mainland to the island or down the VFR route separated.
AirServices should start thinking of charging per hop for each flight that involves an airways clearance,
Yes and and for the same reason lets charge every GA operator whether pvt or chtr who wants to fly through a capital city CTR.
