Actually, when in T/H a quick tap on the brake peddle while going down hill tells the trans controller that it should maintain that speed. It down shifts to hold that speed - all by it's self. Works real good - surprisingly so. Then again, that's a GM and not a Toyota so maybe that capability does not cross over?
For the OP - if you don't have a T/H button - I'd agree you are much safer manually sticking it in D and not OD. But on the flats you could probably give it a go with little to no down side. Just don't forget to flip it back to D on uphill grades or to pass.
If you have not be doing regular trans fluid flush's on the truck, I would 100% do it before the tow. Your truck will thank you for it! Power back flush, new filter and if you can $$ go with synthetic fluid. I'd also put synthetic gear oil in the rear differential as towing will heat them up.
jb