My example of "damn I wish I had more DR":
I went to Munich last May, to the Champions League final. We spent the day walking around the city, taking shots of the colorful fans. Many of those shots were "stolen": you don't want that group of drunken monkeys to know you're taking pictures of them. There shouldn't be any problems, but there could be, so better be quick and low-key, just in case. So auto-exposure it is, and the camera gets to decide where to put the shutter speed.
Say there's a group of people under the shadow of a tree, and they would be properly exposed at 1/100s. If the camera goes to 1/250s, you can still push the image in post and it will look nice. But if it decides to expose for the sky or the building in the background and chooses a faster shutter, you end up with an unusable shot.
If instead of a Canon we were using something like a D800, D7000, or even a D3200 or a NEX-5N, we'd have 3 more stops of DR at our disposal. Even at 1/2000s, that same shot should would end up perfectly fine. Yes, that's what 3 more stops of DR looks like. We probably wouldn't have bothered with auto-exposure: just set the shutter at 1/1000 and fix it in post. Yes. Because you can.