So I’ve found out that the fact that heights doesn’t bother me on their own, climbing a roof in the dark adds the terrifying aspect of a surface that slants the wrong way to the equation. I hate climbing roofs in the dark.
I, however, conquered my fear and climbed the roof in the dark, and have now mounted that dipole I bought on my roof. The fact that I barely conquered my fear is the reason for the suboptimal mounting configuration, as seen below:
The rest was a blissful piece of cake in comparison; installing myself in my shiny new shack and pulling the coax down through the attic.