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Any thoughts would be appreciated.
my advice: go to college, get a sought after degree that's employable in the business world, and nail that first good paying job. don't let his desire to be a rock star derail his future earning potential. once he has that great paying job, enjoy playing music to the extent that it doesn't interfere (too much) with career forward mobility
when he has the $$ he can buy the toys ... and he won't be forced to start back at ground zero when the singer OD's between sets at some dive in Milwaukee
unless his goal is to become a studio session bassist ... and then he needs to get his Masters from a well respected music school (hmm ... maybe Berkley?) so he's well grounded in his playing as well as his theory, and in the process of earning that degree he'll have also learned how to apply himself in ways he's not even aware of today
all the best,
R