Actually, I believe they will think a whole lot more before considering going out into the wilderness unprepared.
Most folks do not want to suffer and/or die when pursuing life's interests. As with all such endeavors, it is suitable to become informed of and prepare for reasonable risks associated with activities, and given the opportunity, I believe most responsible people will avail themselves of the proper knowledge and preparations to mitigate such reasonable risks. The key qualifier here is the opportunity to be proactive about it. I don't know too many "experienced" people that would just go pick up an acetylene torch and try to start cutting steel with it, or a table saw, or a gun, or a car. A reasonable person is going to evaluate the situation up front before taking action, and do all they can reasonably to prepare for it. Does that mean they will always avoid the need for rescue? Certainly not, but if they are aware ahead of time that rescue may not necessarily be free, and that there are avenues for them to pursue which will satisfy their obligations should a rescue be needed and payment is authorized, then I don't see why a person so prepared would not contact the rescuers upon determining their services are needed.
In fact, by excersing a little due diligence up front, I expect that rescues might go off a bit smoother, because the forethought required to make the insurance decision would lead to more preparations by the adventurer in other aspects that lend to avoidance of a bad situation as well as better equipped to deal with one.
I don't know as the Eagle Scout in this case would successfully argue his case for reconvening. I suspect that the department/agency would have no problem demonstrating the requisite details of billing associated with the levied fine. In fact, I suspect if they were so challenged, they could easily exacerbate the value and show cause for an increase in the amount cited. It would be better given the information available for the scout and his family to seek settlement outside of court and not challenge the agency. More than likely, the agency had already sought legal consel on the matter and had cleared an excessive fine amount through proper documentation, and was already judgement proof at the time of the citation. The family would be at a serious legal disadvantage in such a challenge, and victory, if any, would come at a high cost in attorneys and court time. They could fight the good fight I suppose, but would it really be worth it, when they could settle for less than 1/5 the face value of the fine?
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The ultimate result of shielding men from the effects of folly is to fill the world with fools.
-- Herbert Spencer, English Philosopher (1820-1903)