Glad to hear that you made some sort of contribution to him.
Upward looking portraits aren't supposed to be 'correct' but it does no harm to break the 'rules'.
And in this case I think that it rather turns the tables as he (a person that most people would look down on) is now the one who is doing the 'looking down'. And if that argument holds any water the angle is about right too.
?did you ask him to give any particular type of expression, pose in any particular way etc - would be interested to know as eg the background is unobtrusive
As regards the B&W conversion the image generally seems brighter at the bottom than the top - which tends to focus attention on the bottom (in my view) and I would have thought you would want to focus attention on the top ie his face. Eg the handkerchief (at the bottom) is the brightest part of the image
(It's so much easier to comment on other people's images than it is to get your (my) own right
)