As far as meeting that 50-100 flights per orbital, it seems to me that in addition to supplying the ISS and space tourism, another logical opportunity would be short hyper-sonic point-to-point flights -- when your package absolutely needs to get there in 90 minutes. Just slap a FedEx logo on the side of the 'Dream Chaser'.

Of course there'd need to be either a launch site at each landing site, or a large carrier plane to take the 'Dream Chaser' back to its launch site. Similar to how the Space Shuttle is brought back to FL when it lands elsewhere, so that wouldn't be new technology.