Re: Shoebox pulling a Teardrop
I believe that the OD should be used sparingly (if at all) when towing a substantial load. Maybe with a good stiff tailwind or on a long downhill grade, but not often. You also lose engine braking when running in OD, which could be a safety concern. You say you have a 3.89 rear gear; most OD cars have 4.11 gears, so you are putting more of a load than usual on it if you use the OD.
As to the actual temperature, as long as it doesn't boil, there usually isn't a problem. You don't mention losing any coolant, so I don't think there's a real problem. I had to read the post twice to make sure, but you say that it runs cooler into the wind than it does with the wind. If true, that suggests an airflow problem to me.
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