kasha-
Regarding your assumption about the average yeshiva bachur, I beg to differ. Although the average yeshiva bachur does not listen to goyishe music, he has heard of artists such as the one I mentioned, and he knows from his not-so-yeshivishe friends when it is being played at a wedding, so he gets excited. I am a yeshiva bachur myself, in BMG, so I believe I am qualified to make that statement.
As for your second point, I have what to respond but I am pressed for time right now. Iy”h later today.