Bottom line is - he doesn't need to quit.
However -
Dude has had his limelight for well over ten years, and hooked up with a label/industry giant (JMJ) and had his chance to really make it. Dude had a huge radio hit, but now will sell you a verse for 1K or less.
I think he needs to surround himself with different folks, maybe join up with someone tight to form a group and take a different approach to whatever he's doing.