When a tire is difficult to put on the rim, you are much more likely to damage the tube with a tire lever.
Yeah, which is why I'm always extremely careful in doing it. My point in advocating for the inner tube for the first week or so was that I believe it will loosen up the new tire a little bit, which will make subsequent removals and seating the bead and such a little easier. I've had several experiences with seating the bead on a road tubeless that were absolute nightmares, so I ended up buying one of those little tanks that you can pump up with air and then it releases it incredibly rapidly, specifically for popping that bead in.
My MTB tubeless, in contrast, have always been a piece of cake in comparison. I've got no problems using tubeless on MTB, but the problem is a lot easier there because of the vastly lower pressures. Road tubeless, while it feels great on the road, has simply been too big a PITA for me, and I'm off it currently. Maybe I'll try it again in the near future, maybe not. We'll see.