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Oppoinions needed: storage edition

My buddy and I are going to be embarking on another long scooter adventure, like last year when we did the Gambler 500-Illinois on scooters. The Gambler is out of range for us this year, but we still want to go adventure. We will probably be riding 400 miles over the weekend this time. This year, I have a rear rack on my scooter. I’m too cheap to buy an actual top case, so I’ve got two options.

Option A, old Craftsman tool box:

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Option B, milk crate:

He tool box is more interesting and offers dry storage, whereas the crate has the advantage in volume. What say Oppo?

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