I have had to do this a couple of times on car camping trips. Even if not raining, the first thing I do, after donning my personal rain gear, is put up the dining fly. We have a very sturdy First Up fly. Once that is done, I then unload free-standing tent and ground cloth. I then set the tent up under the dining fly and attach the tent fly to the tent. I also attach the ground cloth to the bottom of the tent with large binder clips. Then, in a coordinated effort, we put the tent up in the proper location and very quickly stake out the fly and tent corners. We have a 3 season tent that stays very dry even in major storms and has a good sized vestibule for storing wet boots and rain gear. Finally, if we don't think the rain will end by nightfall, we move our sleeping bags, pads, etc into the tent. They are all in water repellent stuff sacks or compression bags so they don't get wet. We keep our food and cooking gear in large plastic totes, so we just move that under the dining fly.
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