EDIT: I did it! • [Black Mesa] Hat & Pizza - 8 Jump Pads (SU...
So far, no one managed to bring the pizza and hat past this part of the game without cheating. This is a proof of concept for an idea that seems to work.
Similar to the first video, I set the push triggers up for one jump pad (e.g. Northern). Done here with cheats to be a bit quicker about it, but the last video shows an approach without cheats.
The tricky part: somehow, the pizza and myself (with the hat) must simultaneously jump on neighboring jump pads. This allows catching both items at the top, as proven in the end. It can't be the same jump pad, as they have a short cooldown for each object they propel.
I did it with cheats here, by freezing the pods so that they despawn on their own. I'll try messing around with other constellations (e.g. letting the item fall from above, have it lie on a pod, or somehow utilizing the conveyor belts for it).