Sam;
It's been tried by aircraft owners for years. It was a grey area (in fact it was called grey charter in the UK for years as well)
7-8 years ago a helicopter owner took a case against the CAA demonstrating his lease deals. The aircraft was one, the pilot another, Counsels opinion was that it was NOT legal and was Commercial Air Transport and therefore required an AOC, that owner's aircraft went on to an AOC pretty quickly.
I believe it still happens in the UK, normally on N registered aircraft where the oversight within Europe is difficult to manage (I'm talking flying activities, not maintenance etc) Certainly our insurers have stated that in the event of a claim arising from such an activity they will probably not pay out as the aircraft may be covered for commercial operations, but the Munich model does not ensure that the CAT requirements are met in any way and the flight will have been illegal, allowing the insurers to walk.
That is my experience as a current Chief Pilot and Head of Operations for an EASA AOC.
SND