[zamadatix]

Not familiar but like the spirit of the idea. At first glance from just the material you provided it'd have to be a lot closer than 100km apart, 30:1-40:1 seem to be typical ratios with 70:1 being cutting edge and winch launch height seems to top out at 3000 ft (less than 1km). Not to mention for a lot of travel the ground isn't flat which can be problematic even in the direction there is an average decrease in ground height.

Flying in good conditions may be an easier problem to solve than driving in good conditions but the issues seem to move towards what happens in the bad conditions. It's not like you can just hit the brake or park on the side of the road and continue later when the system detects a current or upcoming problem. Even if you get it so 99.99% of flights are in favorable weather and wind without piloting issue a 1 in 10,000 chance your glider is going to make an emergency landing or worse is not good enough odds, especially if it's multiple flights each way. And that ignores the problem of the service being unavailable if certain weather conditions aren't met, so the backup transportation option is still needed at a moments notice in full force anyways.

Then, much like self driving, there are the regulation issues https://www.ssa.org/glider-pilot-ratings/ which would be their own challenge to change and require you solve them before the business can even get it's chance to get going.

That being said I like the concept, just not sure it's really any easier. Perhaps we should just build the missing rail instead :).