As to this incident, it is covered by the Montreal Convention and thus OP may collect the lesser of the cost of repair or the fair market value of the laptop up to approximately $1,650. FMV matters with a laptop because their value plummets as soon as you plug the thing in for the first time.

As a practical matter, it sounds as though this is an employer-owned machine. In that case, have your employer deal with it. Your employer may have coverage, choose to bear the risk, or pursue UA.

On the broader issue, if all other options failed, I would pull the laptop out of its case, wrap it in a jacket and stuff it into the OH. Chances are it's safer and going to be held in place. You can then gate check the empty case and not worry about whether it gets banged around.