A "trailering regen" setting, as in a real down-the-canyon-with-a-load engine breaking would be great! The battery can take at least 135kW at a SuperCharger (empty) which is more than the motor in the car can produce during regen, so yes, you should be able to recoup lots, if not all of the potential energy you used on the way up. Problems w that scenario come with cold, a battery that's already charged, or a car (EV) that's not programmed to take full advantage of the situation, in which cases you will need to use the brakes, maybe a lot! Regen is pretty much gone w a full battery, as is necessary.
Sorry to hijack the thread. I just drive these hills everyday and know that for the short hauls, it's more of an issue than aerodynamics. If you are trailering cross country, then aero is more of a consideration. As is unhooking so you can SuperCharge!