[Leherenn]

A winch gets you maybe about 1/3 of the cable length (and thus strip length) at best. A typical cable length is between 1 to 2km long. Let's say you can gain 500 m height. A glide ratio around 50 is probably on the higher end of what's achievable, so you're looking at 25 km of range. That's before you account for wind, that the world is not flat or the fact that you don't start your landing at 0 m, but more like 200/300 m from the ground.

Honestly, for short ranges, you're much better served by electric planes, or gliders with a self-launch motor. Small strips and winches don't go together.

[TheOtherHobbes]

You can get almost infinite range on hot days by riding thermals.

This assumes thermals are available in the area (some days are better than others, as are some locations), and the s/w knows how to ride them.

But that is a much harder problem than just launching and gliding.

Also, gliders that could carry even a handful of passengers + baggage would be huge, and likely far too heavy for a simple winch lift.

As for the automation - airliner flight is more or less a solved problem, for flights in good weather that don't suffer any emergencies.

It hasn't been taken further because most passengers don't want to fly without a human in charge. And also because the edge cases - unexpected turbulence, difficult weather, mechanical failures, unruly passengers, software failure - happen often enough to be a problem, and they need someone trained on board to take over.

Otherwise people die. And that's very bad.