Hi Zach,
Regarding coverage, it is true that the HD radio signal is weaker (about half the coverage of a station's analog signal). I am not familiar with WJSU's signal contour but I would guess that their HD signal would be enough to cover Jackson and most of the suburbs. I can receive HD signals 50-60 miles away on my Boston Acoustics Recepter stereo. However, this requires tuning of the antenna and these stations would not come in consistently in a moving vehicle.
There is no clear answer as to how much an upgrade to HD cost for a station. I've heard that the initial investment is small, and that iBiquity requires license fees once the technology creates profit for the station. Others have mentioned that the costs are expensive but that could be a bias against the technology. NPR and the CPB are providing grants to public and community stations to encourage upgrades. This allows for more NPR programs with the additional subchannels. The technology costs have decreased significantly over two years. Initially, HD receivers costs $599. Now, you can purchase one for $99 after rebate from Radio Shack.
HD radio provides more dynamic sound. I can hear more detail and additional high and low notes when listening to classical music from my local NPR station. The sound is more 3 dimensional and dynamic than analog. Also, a local college radio station broadcasts many live jazz performances and I can hear more background noise of an audience and a concert hall setting. However, better sound quality is not what will convince the consumer to adopt this new technology.
Most classical and jazz music is recorded with the intent of being played on a CD or in a stereo system. This is where HD shines. Pop music is manufactured and tweaked for analog radio with additional sounds removed. I do not notice any difference on a pop station with an HD signal. Some hip hop, urban, and new country sound slightly more dynamic.
With all the other examples that you mentioned (satellite, radio, iPods, internet streams), local radio has one distinct advantage in that it is local. People want to be connected to their local communities. Subchannels allow the ability for a station to broadcast niche formats where there may not be a large enough audience to sustain a full powered station (such as oldies, alternative rock, smooth jazz). This will be the only savior for HD. This is similar to subchannels on local HDTV stations. Local formats (hence additional revenue streams) can be added at minimal cost. When I travel home to Mississippi, I turn my XM off so that I can check the local stations and catch up with my community. However, I noticed that most of the local stations in the Starkville/Columbus area are either urban, pop, or country with many stations of each. It also seems that most stations are either voice tracked or rebroadcasting a satellite feed. I usually end up listening to the smooth jazz station WKBB 100.9 out of West Point which is also a satellite format.
I seriously doubt any station in Grenada would upgrade to HD as it would not be a smart business decision. Also, since most of the local stations such as B 100.5, WONA, and Bob 99.1 FM rebroadcast satellite feeds, there would be no improvement with sound. The old law of physics, garbage in equals garbage out still applies here. The satellite feeds are not HD quality to begin with and therefore the end result would just be upconverted analog that would sound the same. Regarding subchannels, there may be some potential. With the flat terrain of the Delta, the signals may propagate to cover a large area. Although I don't see this happening anytime soon if the costs are high.
The best we can hope for is that Mississippi Public Radio upgrades their statewide network to HD. This would allow them to have two additional subchannels. One channel could be music programs dedicated to preserving Mississippi's culture and heritage such as blues, folk, country, soul, and other stuff that can not be heard on local radio. Another channel could be a 24 hour news, talk, and information format with statewide news breaks at the top and bottom of the hour. It seems that many local stations are now automated and this could be a valuable addition. I would be willing to support the upgrade in any way possible.