Basically, a truggy
Bobbing is easy (relatively)...dovetailing will be the harder part, since you need to decide where to take the pie out of the bed to tuck the tail tighter...IMO, a dove job on a pickup bed generally looks hacked. It is FAR easier on a Jeep due to the design of the rear.
The best look will be at the bedside seam...that keeps the floor ribs parallel...but dealing with the wheel tubs will make it challenging.
The flatbed will be FAR easier....or just a simple bob job.