I don’t think Charlie is on a wind up here at all. I reckon he probably knows the answers to the questions he’s asking, but what he’s doing here is getting you to explain properly the answers to some of the fundamental flat earthers points about how things don’t make sense, rather than just going “because it is”.
Anyway, regarding the air moving thing, the air above the earth moves at the same speed as the earth because frictional forces acting on the bottom of the air layer drag it along. It’s only slowed down by the frictional force from the layer above moving slower. But at the top of the atmosphere there is no resistance to slow the air down, so it will be accelerated by the layer below. Working back down, even if you started with all the air at rest, it would all eventually be accelerated up to the speed of the earth because of the lack of any resistance at the top edge to stop it doing so.
With the train, as suggested the boundary layer is dragged along at the speed of the train, but the difference with the earth is that there is lots of earth and other things not moving at the speed of the train where the boundary layer of air is stationary – this serves to slow down even air quite near the train. Of course it’s all far more complex than this with turbulent effects, but clearly totally different to the air moving with the earth.
How did I do Charlie? Any obvious holes in that?