Yes, the ability for air to weep from the high pressure side to the low pressure side is proportional to the pressure differential. But there is a differential pressure at which the seat will completely seal off and halt any further pressure rise so yes and no
I'm sure it depends on the specific scenario, but in most cases, I expect it would. An air rifle maker recommended that, if the rifle is to be stored for a while, it's a good idea to shoot it down to the fill side of pressure. Not the same as your question, but it suggests to me that pressure at or below the reg setting is best for longevity.
In my Impact MKII yes. At 155 bar mine will creep 5 bar in about a minute and a half, it does not go any higher even if left overnight. At 140 bar creep is 1 bar or none at all.