The future of a lot of media, not just radio, seems to be up for grabs.
The idea that wi/fi plus internet ratio stations will outshine terrestrial (HD maybe) radio is not for sure.
The courts gave the right to music corporations to charge payments to internet radio stations that are very punitive, and there is speculation most of these will just shut down.
In a related matter, I was shocked to find that a Blu-Ray player I installed on my computer refused to play a purchased Blu-Ray DVD saying that my video card was not approved. Even if I shelled out the cash to change my (perfectly good and expensive) video card, I found info. on the internet that my computer monitor might also not be found sufficient and the Blu-Rae would still refuse to play.
I was in Best Buy the other day and overheard a conversation between a sales-man and a lady asking about DVD players. The sales-man told her to get the Blu-Rae since it was the latest and the others were being phased out. In other words, over time, all DVDs will become like the one in my computer, playing approved DVDs on approved video cards on approved monitors only.
So back to the HD radio, you might think you can escape to the internet radios via wi/fi, but if the average person pays little attention to DRM issues, which seems to be the case, we are all doomed over time.
Oh, and one more thing, satellite ratio is now one company, with Sirius having bought XM. The radio mini-TIVO's, as a result, haven't improved one bit over the past year - year and a half. You are still very limited in the amount of hours you can record. And why is this? A combination of a lack of competition now in the satellite "industry" (can you call an "industry" a single company?) and pressure from the big music corporations.
In summary, enjoy what freedom you have now with music (and TV shows and movies), as it will continue to diminish over time.