Seth, you asked about the DR's windworthiness compared to the MSR Hubba. I had both tents set up on my lawn hoping for an extreme weather event, but it was the wrong time of year. After waiting a week, I began an eBay auction. Now the Hubba's on its way to some happy purchaser in Japan. He's happy, I guess, because he doesn't know what he's missing. The Hubba and the DR look so similar side by side, but I found Shires' creation so far superior in almost every category that I couldn't find a place for the Hubba in my gear collection.
The Hubba can't be supported by vertical hiking poles, as my late-model DR can. It's back wall is very upright, with a short fly protecting it. That's not a very wind-shedding design, IMHO. In a strong, sustained wind, I'd want to pitch the Hubba's door into the wind instead, since like the DR's, it's aerodynamic and can be staked quite low to the ground to minimize drafts. But that means the Hubba's only door must stay closed (no views) and is facing the wind (possible wet exits). The benefits of twin doors and a symmetrical shape are shouting out to me here, especially since wind direction can and does change as a thunderstorm passes over.
The DR seems so much more spacious than the Hubba that I was surprised that MSR's tent was larger in one dimension. Its cross ridgepole is about twice as long as the DR's, which gives the first impression of plenty of space at head level. The problem arises as you look down, though. With a wide ceiling and a narrow floor, the mesh walls are almost vertical. When I sit up inside, that leaves only about an inch between each of my size-L shoulders and the mesh walls. In a very buggy area, it's easy to imagine mosquitoes landing on the mesh and biting me through the mesh as I brushed against it.
Unlike many other folks, I just wasn't impressed with the Hubba. The color might be perfect for stealth camping in a pumpkin patch, but it would wear on me in time compared to the Tarptent's neutral gray. The Hubba's poles do seem sturdier, but the Y-shape created at the ends by the hubs isn't so helpful when I want a "storm pitch." (It's simple to set up the DR normally, then stake the windward door very low and the lee door higher, with the tent's pole slightly aslant.) The MSR's lack of hooded peak vents seals the deal for me.
The Hubba seems like design stretched too far, intended to make a traditional tent (with double walls, reinforced corners and big zippers) as light as possible. In contrast, the DR is an ultralight tarp made as comfy, sturdy and tent-like as possible.
I've probably finished my backpacking for the season here in Colorado, but I intend to put the DR through some extreme weather tests in my Extreme Yard this winter. I'll keep you posted, since this forum was so instrumental into introducing me to this great gear.