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There is no reason to take it out of overdrive when towing. Especially when towing a fairly light load like you have on there. Maybe 8000 pounds would be my guess.
As long as it's not "searching" for a gear, running in Overdrive is fine. I usually leave it in Overdrive until it starts to pull hard and RPMs are down around 23-2400 and then manually back off the throttle and push the button to turn off OD. Cruises around 28-3000 and never needs another gear change. I haul 4k and pull up to around 6-10k. I run only 4.30's in all my V10's.
Rezvani's Latest Post-Apocalyptic Monster Is a Ford F-150 Raptor Underneath
Slideshow: Called the Fortress, the 850-horsepower pickup combines Raptor underpinnings with military-inspired features, survival equipment, and a starting price of $285,000.