Re: Supersonic problems
It's a big ball of Problems from my understanding. Aerodynamics is a big Problem, since stability in the Environment is not a common Feature (turbulence at supersonic speeds is a b&tch!). Material science is also a killer - things travelling at supersonic speeds get very very hot when you try to slow them down with drag. Thats why landers always come with a heat shield, it's the heat shields job to burn away during the descent so that the spacecraft doesnt have to. Determining height and velocity etc behind a shockwave also isnt easy, as it messes with your pressure calculations/Radar telemetry/etc., so determining when to release the parachute is a problem (see the Mars lander Schiaparelli)
I'm sure there are a tonne of other complexities involved, but those three are a good starting Point! ;)