You will likely get varying opinions and a bunch of "facts" to support those opinions, so I'll give you mine.
NEVER tow anything in Overdrive that surpasses the "payload" of the vehicle you are using. Like my PWC, weighs less than 1000lbs total, wet, trailered...and my Tundra's bed-borne payload rating is 1000 lbs (half ton). I tow it in Overdrive often and have had no issues. Anything heavier and I will leave OD off, period - no exceptions.
Apparently, OD is usually a gear that is hung way out on the end of the cog set and is the "weakest gear" in the transmission. But it's my opinion that no owner's manual anywhere that I've ever seen ever says to disable OD when the bed is full (meaning maximum payload) so I take my chances with lighter tow loads - even though I probably shouldn't. I also use OD when towing my utility trailer (about 500 lbs) with my lawn mower on it (also about 500 lbs).
Another reason not to "tow" heavier loads in OD is using your tranny/engine as a brake-helper. If you're in Drive, your engine and tranny will assist you in slowing more than being in OD would.
I don't plan on towing much with my T4R since I do still have my Tundra. Even with 135k miles on it, and years and years of towing (from 1000lbs to 6200lbs), she's still hanging in there like a hair in a bisquit...but I do disable OD on all but the lightest of loads.