We're (much?) closer to Fully-Self-Flying planes than FSD cars because the problem space is - perhaps counterintuitively - MUCH smaller to tackle. And we have a lot more experience tackling it.
Additionally there could easily be remote pilots as backup in case of catastrophe (See remote piloted military and border patrol UAVs)
And pulling a parachute at 1000'+ altitude actually has quite a bit of precedent (See https://en.wikipedia.org/wiki/Cirrus_Airframe_Parachute_Syst...)
Now... There's probably a lot of cultural and regulatory reasons why the "string of automated glider ports" idea will never come to fruition.
But... As far as technical hurdles go, there's not much new technology that would need to be invented here.