What are the most common reasons that cause an aircraft to depressurize while flying? For example, a broken window, a failure on the Outflow Valve, etc.
The most common failure leading to depressurization I've personally seen is a pack/air cycle machine failure. The equipment that takes pressurized bleed air from the engine, cools and expands it. I've seen it happen two ways. 1) The aircraft is dispatched with one pack on MEL and the second pack fails in flight or 2) The aircraft is flying at high altitude, 1 pack fails, the other pack switches to high flow mode and fails soon after.
Pack failure is by far the most common I've seen. But have also seen a couple failed fuselage skins and a few burst PAX windows. Typically door leaks are enough to be noisy as heck, but not depressurize the aircraft.