Blackhand, I believe your judgement of Gerald is pretty accurate. I personally believe that Gerald and other mavericks of his ilk are their own worst enemies.
To carry out an ambitious, locally-disallowed, seaplane launching exercise from a towed trailer, in a highly-regulated industry, without inviting regulatory inspection and approval of the method, prior to carrying out that exercise, seems to me to be classic maverick and ill-disciplined behaviour.
Given that being an operative in aviation requires total discipline and strict attention to regulatory requirements, actions such as Geralds original infringement action, indicate that he was prepared to work outside regulations, and outside any regulatory scrutiny.
Such actions are the equivalent of confronting a cop who has just pulled you up in your car for a trivial offence, and then jumping out and lambasting the cop for having the temerity to do so.
There are many people in this world who have power to create grief for us, and to inflame them with actions and words seen as outside "the regulations" to them, only inflames an already volatile situation created by our own actions.
In these cases, the submissive, "Yes, Sir"... "No Sir"... "Three Bags Full, Sir"... works just fine to deflect these regulatory peoples aims to less costly levels.
However, there are many people who see regulatory constraint as a severe impediment to their own independent aims... and Gerald would almost certainly rate as being in that group.
As a matter of interest, I do know Gerald personally, and have had business interaction with him many years ago, in the farming environment (in which he was raised)... and I believe that many people of rural background are excessively independent, and chafe at the restrictiveness of regulation and external discipline.