PeroK said:
Although there are some clever solutions presented here, this problem was solvable directly, without any insights or clever shortcuts.
Final shortcut.
We have seen
elsewhere that the horizontal displacement of a projectile is given by the, relatively unknown but oh so useful, equation $$\Delta x=\frac{1}{g}|\mathbf v_f\times \mathbf v_i|$$ where ##\mathbf v_f## and ##\mathbf v_i## are, respectively, the final and initial velocities. The vertical component of the velocity is a function of height and can be found quite easily. The approach is to find expressions for the horizontal displacement of each object and set them equal. Clearly, the expression for object 1 has to come in two parts because its velocity changes discontinuously upon bouncing.
Let ##u=v_1## speed of object 1 and assume that "down" is negative.
Object 2
##\mathbf v_{\text{2f}}=\{2u,-\sqrt{2g(H-h)}\}~;~~\mathbf v_{\text{2i}}=\{2u,0\}.~~##Then,$$
\Delta x=\frac{1}{g}|\mathbf v_{\text{2f}}\times \mathbf v_{\text{2i}}|=
\frac{1}{g} \left | \{2u,-\sqrt{2g(H-h)}\}\times \{2u,0\} \right |=\frac{2u}{g}\sqrt{2g(H-h)}.$$
Object 1
For the "going down" leg (a),
##\mathbf v_{\text{1f}}^{(a)}=\{u,-\sqrt{2gH}\}~;~~\mathbf v_{\text{1i}}^{(a)}=\{u,0\}.~~## $$
\Delta x_a=\frac{1}{g} \left | \{u,-\sqrt{2gH}\}\times \{u,0\} \right |=\frac{u}{g}\sqrt{2gH}.$$ For the "coming back up" leg (b),
##\mathbf v_{\text{1f}}^{(b)}=\{u,\sqrt{2g(H-h)}\}~;~~\mathbf v_{\text{1i}}^{(b)}=\{u,\sqrt{2gH}\}.##
$$
\Delta x_b=\frac{1}{g} \left | \{u,\sqrt{2g(H-h)}\}\times \{u,\sqrt{2gH}\} \right |=
\frac{u}{g}\left[\sqrt{2gH}-\sqrt{2g(H-h)} \right].$$ Putting the expressions together, $$\begin{align} &
\Delta x=\Delta x_a+\Delta x_b \nonumber \\
& \frac{2\cancel u}{\cancel g}\sqrt{\cancel{2g}(H-h)}=\frac{\cancel u}{\cancel g}\sqrt{\cancel{2g}H}+\frac{\cancel u}{\cancel g}\left[\sqrt{\cancel{2g}H}-\sqrt{\cancel{2g}(H-h)} \right] \nonumber \\
& 3\sqrt{H-h}=2\sqrt{H} \nonumber \\ & H-h=\frac{4}{9}H\implies h=\frac{5}{9} H.
\nonumber \end{align}$$No quadratics, no use of symmetry, no kinematic equations, no time-of-flight considerations.