I again read your post.
So I think the “least” and “greatest” have to do with priviledge not status. In this context those of us who are alive during the rapture would be the greatest” in priviledge over Paul who would be the “least” in priviledge as he only taught and looked forward to the rapture that maybe you and I will actually realise.
Won’t Paul be raptured?
It says the dead first, then those who are alive.