The more massive the piston, the less likely you know the internal structure very well, i.e. the location of seams/fissures that could rupture unexpectedly. Maybe it becomes a non-issue after the cylinder is filled and the piston is "floating" with uniform pressure around the sides, but it would sure be worrisome during the excavation.
I'd not worry tremendously about the static seals along the walls and floor of the cylinder, but the rolling diaphragm piston seal...working at several tens to a hundred bars...across a meter or three of radial span? That's a pretty tricky job, given the seal will be formed in-situ, so no real chance of using cured elastomers. Not saying it's impossible, but we use rolling diaphragms in our products, and design for 100-200 psi is non-trivial in a long-stroke rolling diaphragm.
I'm also curious as to how uniform in density the piston rock will be. They show a system of rollers to guide the piston along the upper edge, but if the rock is heavier on one side, how many megatons do those rollers have to be designed for, and will the seal still get pinched if the piston tilts?