I'd find it a bit disconcerting but I suppose people can get used to anything if the are exposed to it often enough.
To a degree. I still have a bit of a fear of heights, but when I know there is some form of a security blanket I have no problems looking straight down at the ground from hundreds or thousands of feet up.
This does bring to mind an amusing tale of my first jump though. When we started to approach our jump point my instructor flung up the door of the plane and called me over to look out the door to where we would be landing. There was one slight technicality though - I did not have a chute on my back, it was a tandem jump and the instructor was wearing the chute and he had not hooked onto me yet. So I very gingerly crawled over towards the door keeping my center of gravity VERY low and quickly and ever so slightly peeked my head out the door before immediately pulling back.
Of course the instructor got a bit worried that I might freeze up or something after seeing this and made a comment long the lines of "you are going to be jumping out of this plane in a couple of minutes, so you better get over this". My response was "well I don't have a parachute on my back, and until I do I am going to take EVERY step possible to make sure I do not leave the plane without it".
He then proceeded to latching onto my harness so we could jump. Quick bit of back story - When we were on the ground just prior to rehearsing our jump he had asked if I wanted to dive out of the plane, or if I wanted to do flips. I told him I wanted to do flips, so he then explained that the harder I pulled when it was time to go when we exited the plane the more flips we would do. So back to the jump.
I am now all strapped in and have no problems with that door that I was so timid of previously. We get to the doorway, I put my feet out on the bar, he counts to three: one.. two.. three!! and on three I lunge forward with everything I have.
A tad over a minute later I pull the chute and in the relative calm of being under canopy I hear this hysterical laughter behind me. Of course I ask "what's so funny" and my instructor says "I have been doing this for years, and I have NEVER been yanked out of a plane so hard in my life! here i was expecting you to freeze up, did you ever prove me wrong!" and of course I had to tell him again that the chute on my back makes all the difference in the world.
So long story, but hopefully amusing, the point of it (other than entertainment) as it applies to this thread is that as long as there is glass between me and the ground and I know it is structurally sound, I am cool with that.