enabling or caring?

It is  sometimes so hard to decide if I am enabling or just caring an example : when my son lost his wallet with his debit card, license etc... I told him to take care of it and do what he needed to do such as call the bank and report his card lost get online with dmv for replacement license etc... so what does he do? stays at his friends house and finishes watching his movie hello? is anyone home upstairs?  Someone stole your wallet ( even this is in question because he was obviously too drunk to remember if he lost it or it was taken) and they have your license and debit card and you sit there watching a movie does this make ANY sense?  anyway the point is he is clueless ( yet he thinks he knows EVERYTHING)  So he has to borrow one of our credit cards to order replacement license he cancelled his debit card and will get a new one within 10 days and yes I will expect full repayment for the license I am not paying  for it  but my question is would you consider that enabling by lending him the credit card also by looking up the number for the bank  for him to prevent someone from cleaning out  his account with his debit card because I look at it as trying to stop the ongoing cycle of craziness which will eventually trickle down to his father and I because if all his money is taken I will not be getting paid for the insurance money he owes me so even though I am protecting his interets I am also protecting my own so is this enabling or caring?Where do you draw the line? Oh and by the way after all of this his friend calls him and says we found your phone and wallet in so and so's car so it seems after all there was no mystery thief just a dumb drunk.