From Montréal to Portland in 2 Hops

Last week, I travelled from one side of the continent to the opposite side of it. By all accounts this should be an easy thing. People are travelling this route and longer distances everyday. But a small delay (30 minutes) in the first flight, completely disrupted the plans. What was supposed to be a 10 hour trip, took over 24 hours, and involved a very creative path. What is not obvious in my description is that other delays should be added to the 30 minute delay: waiting to pick up luggage, going through US customs, going through security, etc.

In an age when I can order something online and have it shipped to me from across the world in a couple of days, why can’t I travel with that same efficiency?