It all depends on how he does it, what the stall of the torque converter is and how the software controls it.
Most of the newer (less than 2 years as you state) just simply won't shift into the other gear, even if you put the shifter in reverse while moving forward, until it's ready so really not possible to do much damage. The transmission just simply does not obey the operators commands until it's safe to do so.
If the stall speed of the torque converter is say 1800 RPM and he's shifting D-R at a vehicle speed that is below the 1800 RPM stall speed, also not much damage to be done assuming the transmission actually obey's the operators command since it's below the stall speed of the converter so it's really difficult to shock the driveline much when there's a "soft" connection through the torque converter.
If the transmission obey's the operators inputs and the operator is driving like an idiot with the engine at/over stall speed while changing directions then it's going to be really hard on parts.
With a bit of practice on a given truck, you can get good at timing the shifts so that as you roll into the pile the transmission engages reverse as the truck comes to a stop and you just back up. Reverse to drive is a bit more tricky, but the same idea applies