It all depends on the steepness of the hill and how abruptly it ends. A small hill with a tabletop will require more speed then a sharp up and down. Damage to the truck is a byproduct of your landing. Harsh landing=damage. Back in the 80's my dad used to jump my bronco over other trucks, hence Airborne69. It has maybe an inch of lift with 33's. Aside from the occasional broken driveline, no major damage occurred due to the soft and sloped landing.
The best advice would be to test out the jump spot multiple times before really going for it. Start slow and work your speed up as you feel more comfortable. A sideways lip at the top of the jump can ruin your day. Make sure that the truck doesn't dip down to one particular corner. Landing on a single front tire is probably the worst that can happen.
Goodluck, wear your seatbelt, and take lots of pictures!