Interestingly enough the height aspect never really bothered me even though I'm nervous on ladders. I was a traffic reporter. The chopper pilots were veterans, the airplane guys were basically kids working to collect enough hours to get a better aviation job.
We had a couple of :"incidents" that in hindsight give me pause (declaring an emergency into the old Navy Airfield north of Chicago to avoid a thunderstorm). A about a year or so ago wife and I took a trip to Las Vegas. The trip included a helicopter trip to the north side of the Grand Canyon, basically tribal territory. I enjoyed it tremendously. We landed in an area near the Canyon, and had a chance to go walk on the Glass Bridge over the Canyon. That was a bit nervy at first, looking at that big drop below (We were safe, but the illusion was interesting.
Back to the flying experience. Chicago does an Air Show every Summer on the Lakefront. One year some promotion person had the bright idea to have the "Air 78 Squadron" do a flyby down the lakefront. I'm not sure how they managed to actually get that passed the FAA. They did make us fly single file only along the route (3 Cessnas and a twin engine plane from the flight crew). During this I was supposed to "chat" with the radio station anchors doing the radio "play by play"
Anyway we're heading down over Lake Michigan at about 500 feet and I'm describing whai I'm seeing. One of the producers tells my wife who was managing the broadcast "he sounds good" Her reply, "he's ****less"