Plains fly over the obstacles? Thats kinda the point? Also i may have underestimated the amount of people flying in the us cause in europe one flight a day is completely normal for destinations at this distance. Of course if thousands of people want to move between these two locations each day a regular shuttle could make sense but you cant just ignore the distance, 2.5 hourse is a very very best case scenario. Planes can also fly boutta 1000kmh but that doesnt mean a place 1000kms away takes 1 hour, 1.5 to 2 hours is completely normal for a journey like that without accounting for all the flight related hassles. Of course thats a huge upside of trains but you cant just freely apply train to everything. This is very likely a place where a highspeed rail connection would make sense but nothing is ideal instantly. Not to talk about how these cities would have to improve their own public transit to be able to connect to a wider network efficiently.

planes missing connections is rare and the airlines provide some degree of compensation, Amtrak has no such reputation.

Having to plan connecting flights is a thing.