>>2053115NTA, but you are largely right IMO. That being said, the process of the skirt needing to ride over you is probably going to be a lot rougher than you are estimating it. If the craft needs to "pitch up" to get over top of you, then a lot more pressure is going to be locally present there.
Like a book has a certain pressure to it lying flat, but if you prop up one corner, there's now going to be a lot more pressure on that corner and the opposite edge.
Even if the hovercraft can, eventually, equalize the pressure across the entire bottom, there's going to be a disequilibrium at the moment when the hull's momentum starts deflecting.