For two-way communication, digital is undoubtedly superior to analog if the sampling rate and quantization are high enough. The two way component allows error checking and/or correction to monitor the data stream, and resend bad packets if necessary. At the least, it allows monitoring of the stream to reduce data rates if a particular pathway becomes problematic. Frequency-hopping technology would allow channels suffering from interference to be ignored.
In broadcast, it's a one-way trip. There's no feedback from the other end when you have only a receiver on the other end, not a transceiver. There's no error correction or resends when you don't know if the other end is receiving your signal. Instead of signal fade, you get drop-outs. Pick your poison in fringe areas. Of course, the FCC says that fringe areas don't count. Unfortunately, a "fringe area" could simply be in the shadow of a hill or a large building in line-of-sight transmission.
One thing for sure is that the hybrid analog-digital mess created by IBOC doesn't do either technology well. And, the cell companies are building out data capabilities at warp speed to accomodate customers who want to stream audio and video on their cell phones. And, they already "buy" new cell phones every couple of years, so it's not like they have to go out and purchase an expensive new "digital radio". It's part of the package.
The AM frequency spectrum is spectaculary unfit for high-speed data. The FM spectrum is certainly suitable. Optimize the AM signal by going back to wide-band audio, or even C-QUAM stereo. Leave FM alone. If the big boys want more channels, let 'em compete with the on-line providers. That's the simple answer, but it doesn't put any new money in the government's pocket.