Caught between two packing methods after a rainstorm wrecked my bag in Portland

I was walking through the Pearl District in Portland last month when a sudden downpour hit, and my bag's top zipper failed because I had stuffed too many loose items in there without dry bags. My laptop got damp and my notebook was soaked, but my clothes in a compression cube stayed bone dry. So the debate is: do you sacrifice organization for quick access like I did, or do you bag everything separately and just deal with digging? Has anyone else had a gear failure teach them a lesson about overpacking one way?

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