Bear in mind, he used the 12t. Which is what I'd recommend for "the hilly part". And maybe run more voltage but enough less amps to tame the start up.
20s lipo, maybe not, but 20s lifepo4 is pretty close to 60v nominal. Using the slow wind, you'd likely see the amps drop off very quick regardless of your theoretical max, and your amps would remain below 1500w, which can be tolerated by the macs if you are careful about watching the temps.
I would say 12t, and highish voltage for the win. But not more than 70v or so when fully charged. 15s or 16s for lipo? 18s if you stick to a lower amps controller?
But again, a spare motor in the garage would be a very good plan if you run the very highest volatage or wattage.