Just my opinion, but this discussion revolves around a sort of philosophical problem that I find a bit troubling. Please forgive me ranting.
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Excellent thoughts, Andrew - your take on this mirrors mine very closely...
This sort of bass-ackwards focus has become increasingly prevalent in recent years, and I definitely feel blessed to have gotten into the delivery trade long before such concerns were the primary priority...
I liken what's occurring in the delivery business to the phenomenon that has overtaken, and completely transformed, my 'real' vocation - photography - as well... Just as GPS/electronic charting has enabled pretty much anyone with a warm body to take a boat anywhere, the incredible advances in photographic technology and digital post-processing/manipulation have enabled virtually anyone with a decent eye to produce professional-quality results... I spent years learning the craft, and the nuances of how films like Kodachrome and Velvia reacted to light, at pretty much the same time I was getting the experience to acquire a CG 6-Passenger license... Of course, that's not the way it's done nowadays. Hand-held light meters have become as superfluous as sextants, there's no need to get it right in the camera anymore, mistakes can be corrected digitally afterwards, just as easily as a shot of bow thruster can save your ass after a completely blown approach, or cluelessness as to what the current alongside might be doing... (grin) As a result, you and I now find ourselves increasingly competing with many who may lack a deeper or harder-won understanding of the craft, or lack of a fuller understanding of all that they may not know...
I realize many who have chosen more conventional paths, would not understand yours and my views on a subject like insurance, thinking us reckless, or hopelessly naive... And, perhaps they're right... But, my eyes quickly glaze over when reading a thread about "Yacht Delivery Contracts - What to look for?", for example... Over 35 years running boats, and I have yet to ever offer or sign a 'Delivery Contract'... If my reputation, confirmed with a handshake, or my soothing voice on the telephone isn't good enough for the client, well... he should probably be looking elsewhere... (grin)
I don't know, I can't help wonder whether the OP may not really be cut out for our line of work... Funny, most everyone I know running boats simply "fell into the business" somewhere along the line, a surprisingly small percentage seem to have made a conscious decision to become a delivery captain...
Not to mention, I can't imagine anyone I really know and respect in the trade, uttering a sentence that begins with the words "Well,
my lawyer tells me..."
On the other hand, perhaps guys like you and I are the real dinosaurs, and the wave of the future is delivery skippers beginning to learn our craft in law school, or a study of the nuance of the insurance industry...
Grin, bigtime...