headset seems like a bit of a mistake if it cancels out all outside noises as that would be extremely distracting. I dont mind it for a racetrack, rally, etc. But using in both ear speakers is not wise for the road.

I am quite sure a beats or otherwise blue-tooth speaker set would be plenty loud even at speed. Are you going to have symphony quality sound at speed...no, but you could still listen to music. Plus, at idle it would most certainly be loud enough. Putting around town something like this would be perfect.

Ideally you would get speakers custom placed into headrests as the proximity to your ear will matter, but thats a whole nother level.