There will be no security checks on the layovers so the only thing you have to worry about is your first plane being delayed. Quick tip is to look at the manual in the back of seat, There is most likely a map of the terminals in it and you can see what gate your landing at and the gate you need to goto when you arrive. And make a plan of attack.
Customs will happen on the Calgary Side on the way there and the way home. If your flight is early in Calgary go early because the line can get massive.
Denver isn't as bad as you think. I once had to make a connection in 22min a terminal over. It is easy.
Once you get off, make hightail for the center (Walk on the moving walkways and it will be like you are running with out all the work. Once you make the center atrium hit the stairs down to the trams. Hop on the tram you need and it should only take a few min. From there follow the same procedure to the gate you need.
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