I have just purchased a 2014 Street Glide and would like to purchas a Sena SMH5 communication system. Can anyone tell me if the Sena will blutooth with the Boom Box on the Street Glide so as I can listen through the speakers in both rider and passenger helmets and not on the bike speakers.

As far as I know, Bluetooth pairing only works between two devices. Eg, the radio and one headset, so I doubt you will be able to get the sound in both headsets. Also, the radio is more likely to play tunes from your phone over Bluetooth, than broadcast its sound over Bluetooth.

My wife and I use the scala rider G9, and we each have to pair with a phone or ipad. We can't both listen to the music on the same device.

While my bike is an earlier model I have cut into the speaker wire and taken that feed to a FM transmitter (don't just solder in a connection, go the Jaycar and get a proper isolated interfact box). These bluetooth devices have an FM recevier so that allows both rider and passenger to listen and you can use the radio controls etc normally.