With my powerbox fins I've found through trial and error that the brass barrel nut will strip if I hit a rock or similar obstacle large enough to rip the fin from the board. This could open up an argument for and against power/tuttle boxes, but ensuring that the fin is secured to the board to the point where the board is going to be damaged just doesn't cut it.
For my money the fin almost has to be "sacrificial" if you're in conditions where fin damage may occur. Each time I find some limestone

I just hope the fin has taken the full force of the strike. I certainly won't re-enforce the anchor point of the fin with any washer larger than the stock one.
Also when I rebox any fin I won't use too much re-enforcement around the barrel nut for that purpose.