Well, I am no expert...but I keep OD off unless I am on the highway or driving over 50mph for extended periods. Leaving OD on in conditions where you vary speeds above and below the 40-50mph range makes the trans flip flop back and forth from 4th to 5th. This can't be good for the engine/trans. Also, when going up hills your trans tends to downshift to 4th anyway for the extra power and torque, so why not keep it in 4th to begin with. Plus, when going down hills, keeping it in 4th allows the engine to slow the truck down rather than working your breaks. If you've ever driven down a mountain they always advise you to drive in lower gears as opposed to using the breaks. Using the breaks alot to slow you on hills not only wears more on the breaks, but can easily overheat them.
So in my non-expert opinion....keep OD off unless you are doing highway or consistent higher speed driving.