I excelled a little to draw what we had so far in post #1 (vi = 16.4 m/s, 39 degrees wrt horizontal).
As you see, the bar would be moving horizontally at the y level of your buddy if there were no slope. This is at t=vyi/g, by which time x is already over 13 m.
In post #6 you continue with
total time = 2vi sin (a) /g
which comes out of the blue as far as I can see. In other situations a 2 comes in because we can use time from ground to apex = time from apex to ground, but that is not what we have here: catch is at the apex!
So the thing has to be thrown a bit higher up, as you already indicate in your drawing.
Bravo for doing the drawing. But: we were making such good progress in the x-y coordinate system in which g points in the -y direction. Much more comfortable to stay in that system a little more, and look for the angle to throw wrt horizontal. When I look a little longer, I see a theta = a, so I take it you mean wrt horizontal the angle is 39 + a. OK. And the vector pointing to the upper right is
v_i
But the expressions are not correct: vi cos (a+39) should point horizontally to the right and vi sin (a+39) is the y-component, pointing straight up. Also, the curved line can't be right: the bar never ever has a negative vy.
Remember, vyi has already been established and is correct: we can't change it any more. It's the only way to get vy = 0 at the 5.4 meter higher where friend is. Corresponding time is indeed vyi/g, 1.05 sec. That too can't be changed any more! And yes, friend is at the apex of the bar's trajectory in the air.
Now all we have to do is aim a little higher
and at the same time throw a little less hard in such a way
that vyi stays the same. Only the horizontal speed has to change. How much ? Well, so much that the bar is at the x-position of our dear friend at the moment it is moving horizontally (which as we agreed is at time vyi/g).
So we have one equation with one unknown. Solve and calculate vi as well as the angle wrt horizontal !