I'm assuming glider landing gear is pretty tough... landing a tricycle gear aircraft in a random field is a gopher hole away from an accident. Guessing gliders handle rough fields a bit better?
Yes and no... it depends.
I know jack squat about gliders with retractable gear, or tailwheel-configured motorgliders, but I have made over 100 landings in Schweizers with a monowheel main, a skid forward of that, a tailwheel in back, and "pogo" outrigger wheels near the wingtips.
The monowheel will tolerate a lot of side-loading (on grass or dirt, anyway), but there's a limit. And because our ships' main wheels have no shock-absorbing gear (they are bolted to the frame with the axle itself), rolling into a gopher hole or whatever can be unpleasant, if not really harmful to the structure. The most likely damage would be a blown tire, bent hub, or trashed bearing, because the steel tube frame is very strong in that area.
The pogos are not really tough, but they are not intended to absorb landing and rollout energy, so much as to make it easier to move it on the ground. Sure, there may be a little forward motion as either wingtip comes down after landing, but they are plenty strong enough for that.
But I can't recall a landing of mine where I put much mileage on the 2-33's pogos during a landing roll- even if I don't keep the wings perfectly level, the roll is pretty much over before a pogo comes down. In the end, the pogo's most important job is to protect the wingtip in the event of a ground-loop type situation.
The tailwheels do most of their work on the takeoff roll, as far as I can tell, and obviously they are important when tugging the gliders on the ground. The 2-33 has a good castering tailwheel (non-steerable), and the 1-26 has a non-castering tailwheel, which requires a little extra care when landing or rolling on a paved surface.
The skid is sort of an emergency brake... if one lands long and hot for whatever reason, or if a landout has to be made in a very tight space, forward stick will tip the glider onto that skid (which is sort of a leaf spring made of wood, and in the case of the 2-33, laminated with a hunk of aluminum bar stock). On any dry surface, it will stop the glider very quickly, and suffer minimal wear at typical landing speeds.
So even if, say, the main wheel axle failed, the lower frame bent, etc... chances are good that a 2-33 would just skid to an abrupt stop with the tail slightly high. The occupants might have trouble sitting down for a few days, but maybe not. And you'd have to basically touch down in an open manhole to do that much damage.
The more typical worry with rutted fields or fields with stumps or big rocks is hooking a wingtip while you're still moving pretty quickly, or damaging the fuselage fabric or the fiberglass nose bowl. Rolling into a hard-packed, deep rut can also wreak havoc with directional control on the rollout, which could cause a groundloop and possible wing damage.
