
I know the lines are generated by projecting geodesics on a hyperboloid to a plane and the boundary of the disk comes from the asymptotic cone around the hyperboloid, but I just don't see why the projections intersect the boundary of the circle at a right angle.
You need to follow through a sequence of maps. Project the intersection of the hyperboloid $z=\sqrt{x^2+y^2+1}$ with a plane through the origin onto the unit disk at height $z=1$. This gives a general chord of that disk. Move the disk down to the unit disk at height $z=0$. Project the line segment back up to the unit hemisphere (now the segment becomes an arc of a circle orthogonal to the unit circle), then project back to the unit disk by stereographic projection from the south pole (so the arc becomes an arc of a circle which remains orthogonal to the unit circle)!