While I completely disagree with your point here Boo Boo, this phrase you've used here is amazing. I mean, someones point of view can be questionable? Not even Reagan could cook up this kind of brilliance.
To challenge, You can absolutely tell when someone has experienced something their singing about, and you know full well when they have not. If you can't tell, I'd chalk it up to an inexperienced ear, or perhaps some just have a predilection toward distinguishing one from the other. I myself have no issue deciphering when someone is remerabering how they felt when they sing about an issue that has effected them deeply, and when their trying to sing a song note-perfect.
Its like speech writing, some people want to convey a message, some people just want to get to the podium and back to their seat without sturabling over their worRAB or the rug.