im sure that 1940s plug lasted significantly longer than any new plug will

Your torch is spewing flame because you’re feeding it liquid when you angle it like that.

Red ground is all kinds of heresy.

personally i'd prefer a soldered/braised connection to an earth rod rather than just a crimp, but to each their own

Super, glad your still going in now an apprentice and it's amazing doing what you love to do

Stop sloshing around the torch, that's the reason the flame is going crazy like that. That's thermo contracting insulation....Usually crimping is referring to the stuff that you actually have to crimp mechanically.

The black thing is some sort of weatherproof shrink wrap cap?

you'd probably have an easier time with that ground clamp if you had some ear clamp pliers

Do you do anything to seal the penetration, or is it a non-issue with the placement and angle?

Can you PLEASE use an electric heat gun to shrink things? It does the job much cleaner, is a lot better suited to shrink tube temperature wise and doesn't set stuff on fire.