Whew! I feel ya Drew! A fear is healthy; a phobia is usually unreasonable and unhealthy for the individual. I know people who cannot drive over overpasses or bridges.
I don't like ladders. My brother broke his back when a scaffolding collapsed and dropped him 3 stories onto his feet. One can get used to heights but something about tall buildings freak me the F out! I couldn't go to the top of the Stratosphere in Las Vegas- just to the mall level. Years later figured out what was unnerving me so: it was the building swaying slightly and my equilibrium was picking it up! But there's nothing like standing next to the edge of a drop- be it on a cliff, building, bridge or otherwise you can feel that gravity threatening to suck you right over the edge!
And I see very little merit in jumping out of perfectly good airplanes, base jumping, bungee jumping or free climbing. The margin for error is narrow and unforgiving.
A big wind blew a neighbor's window screen up on the street-facing side of my roof last year. It laid up there for six weeks at least until I got the nerve up to go get it. And this was only after I had accidentally flung an entire 25' orange extension cord up on the roof while trying to fish the screen off with it.
So embarrassment overrode the fear.