One thing I noticed, ( with me at least...) the higher up I go , the less sense of height there is. If that makes sense.. I'm no more uncomfortable at 400ft, than I am at 40 ft. In fact a little more at ease. Maybe because the ground is father away.
I did a rappel a few years back off the roof of this 34 story building in Jersey city. Had no problem going over the edge. On the other hand I hate stepping on and off off a ladder from a 2 story roof.
We regularly practice our rope rescue stuff In the old Hindenburg hanger here. 225ft from the inside floor, to the top catwalk. Only un-nerving part is now and then you have to bang on the boards in front of you to make sure you foot don't go through it.
Here I am doing some transverse highline and basket work off the roof line. Love it!