Nah. You've messing up something 4chan worked out years ago. You need a BLIMPTRAIN! Locomotive on rails towing a train of lighter than air vehicles that can detach under optimal conditions/location to deliver their cargo over the last mile.

Yes, then we could put wheels on my grandmother and we would have invented a bicycle badly

https://youtu.be/A-RfHC91Ewc?si=uMjPf00zqbJHfSwn

We are so smart that we can take good things and modify them in stupid ways to make bad things. This is, in fact, very smart of us.

Winch launching is already a thing https://youtu.be/U3ztaJ0yfxE?si=1AjAS8F8-pCaUFZI

Building a railroad over water or through a jurisdiction full of jerks is expensive.

I can see a big winch glider being worthwhile in some very limited circumstances.