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My personal problem with any sort of softbag is that I often walk away from my bike (lunch, dinner, mall, etc.) and they can be cut too easily. Thus why I do my long distance trips with locking solid panniers and trunks.
REI sells bags (mostly purses) that have a steel cable mesh between the layers of fabric (imagine chicken wire sew between the layers), and through the straps. Idea is that people won't be able to just cut your bag to get the contents, or cut the strap and run off with it... Though for a waterproof bag they'd still be able to make it no longer waterproof.