Not being a Scout guy, I can only offer crazy hypotheticals/theoreticals. I always like the idea of having a healthy dose of paranoia and pessimism. I try to visualize the event and invite Mr. Murphy along for comedic relief. I then start to build the kit/pack from there. There is a lot to be said for being Eeyore - anxiety-ridden, paranoid, and pessimistic crazy

My $.02
YMMV
IMHTAO (In my humble, though accurate, opinion)
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"Its not a matter of being ready as it is being prepared" -- B. E. J. Taylor