The way physics generally works with towing (for either ICE or EV) is that you will cut your range down significantly based on any number of variables. Of course this is going to vary greatly based on things like temperature, gradient, headwind, aerodynamics of the load, opportunities for regen, etc, etc, etc....
Range (with, or without a range extender) will be a factor while towing based on all of the above.
Let's just say for shits and giggles and to keep it really simple that you will loose 50% of your normal range while towing XXXX pounds down the HWY on AVERAGE for each of your trips. The question is, will you loose 50% of your range if you have the range extender running and a smaller battery? Well, likely yes, because to your point, you must take advantage of the range extender earlier, since you loose more SOC sooner in your journey.
I think the nuance in the question is really this:
If I have the pure EV Terra and I have the range-extended Harvester Terra side by side towing the exact same XXXX pound trailer, under the exact same conditions on the exact same route, what will be my EXPECTED range for each based on a 50% loss?
The snarky answer is this:
I would expect that the pure EV loosing 50% of its range is going to run out of juice at the 175 mile mark
I would expect that the Harvester EV loosing 50% of its range is going to run out of juice at the 250 mile mark
in reality, i really don't know what we will see with side by side towing of the same weights, bc I am unsure of the efficiency of the range extender and how much power loss there will be through conversion... That is all TBD, but in reality, I don't think I would expect to see HUGE Towing gains in a range extended vehicle. What you may see are a few less charging AND gas station stops on a longer road trip while towing.
Interesting graphic for your consideration while towing 10K pounds in a R1T and a Lightening (from consumer reports):
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