he is clearly not coming to terms with his addiction in any real sense. of course he cried - he is messed up. but him knowing that he is sick, is not the same as him being close to getting a grip on it.
i think you are obsessing over something for no real reason. what does it accomplish to check up on him? you already know he's broke, he's using, and he is not interested in changing things - not enough to do something about it.
do you know why you are so stuck?