I used to do the walkman thing as a teen. I would break the headband off and stuff the speakers in the helmet.
Depending on what bike I ride now, depends on what setup I use. If I am on the 750, I use just regular $10 earbuds from walmart. When I am on my Venture, I plug in my helmet to the bike. I have a headset and mic setup in my helmet as well. I have not justified the little $45 connector from a MP# type plug in to a 5-pin DIN.
Sound quality, I read people complain all the time about quality. Guess what, your not going to get it unless you pay hundreds for a speaker setup and people still complain. In short, accept the fact that they are not nice three-way bass thumping speakers and enjoy it or don't do it at all.

The best sounding setup I have used since a teen was actually the old Walkman with the band broken off. Those speakers had some size to them. My $80 speaker/mic setup is ok but not worth the $80 I spent on them. Just go with a $10 noise cancelling earbud setup for bang for the buck!