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I would guess the vast majority of cyclists use regular cycling shorts, i.e. the pad sewn to it and not use liners.
A good quality pump like the Lezyne, or even the venerable Road Morph, is reliable and easy to use. Probability of failure is pretty close to zero.
Another consideration may be if you prefer to ride into the sun or have it at your back. I personally strongly dislike riding into the sun and am an early rider. Therefore, I tend to prefer W>E if wind is not an issue. If you are an early rider, when you ride into the sun, cars behind you may not see you as easily in early mornings due to being blinded by the sun. If you ride away from the sun, you may have less skin cancer (a major issue with me). However, the reverse is true if you depart camp late and ride until evening.