Guess I'm spoiled by the availability of cheap high-power electrical gadgetry since all consumer-side single-phase electrical in my country operates at 240V (then we have three-phase for industrial applications).

To illustrate, here's an example of a mechanical timer available locally that can handle 3200W for €9.50 - link [UK plug]. No idea whether something like this exists in the US.

The EVSE has a temperature sensor that should shut off if plug temperature gets too high. To cater for people plugging in at outlets in 70-year-old houses whose plugs were never rated for more than a desk lamp. I was under the impression that OP was in a garage protected from water hazards.

I agree with your general sentiment to prioritise health and safety though.

Dear OP, please check the power handling capability of any electrical contraption you implement. And use common sense - don't plug an extension cord in the rain, and don't try to draw 2x EV loads from the same plug simultaneously.