Not really a grey area is it then? As I understand it, if you have an AOC and are doing skydiving operations you don't need the APF Jump Pilots Licence, if you are operating as a Private Operation then your required to have one!
Sure about that?
I think the case might be that, in order to have 'skydivers' being dropped from an aircraft you would have to operate under the APF rules. As far as casa is conserned it is the APF who administeres skydiving, so in the example given you would both need to hold a cpl & be operating under the schools AOC (which also may have to allow skydiving activites (not sure of the finer details in this respect)) and finally the pilot would need an jump rating.