Given the background, this is one of those situations where the old adage " familiarity breeds contempt"
If you were someone he didn't know, that may have not happened, but what I read between the lines is that this guy A) absolutely needed you and probably sold you before you said no, so he had to go to a Plan B and B) because of his familiarity, doesn't observe the lines between personal and professional very well, and C) he IS from New York, and as such will be much less polite and much more direct, which is off-putting. And D) Because he has you as a friend, he probably tries to take as much advantage of that as he can.



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