I've only returned from my first trip several weeks ago and mostly stayed in the west end so my experience likely differs from others. I will defer to others who have more experience. With that said, I was disappointed that there weren't clubs/bars catering to different styles/age groups etc. The live entertainment I experienced was good but you'll almost always get a heavy dose of the classics. Not all bars/hotels always play reggae and when they do, again, it's typically your roots rock and lovers rock classics. You'll find today's dancehall playing in the dance/night clubs.
Some bars, at least in the west end, will play your CD's or songs off of your IPod/mp3 player which I'm keeping in mind for next trip.
Trust me though, you won't miss it that much and you'll find many other reasons to come back.
