Don't get a Tacoma for this - a Kimbo weighs upwards of 1k lbs, right at the limit of a Tacoma's payload capacity. Add in fuel, people, water, anything else heavy and you're above the rated capacity before you know it.
EDIT: And yes, the insurance company will weigh your equipment after an accident.
To get much beyond the 1 to 1.5k lbs PAYLOAD capacity, you need to move into a full size truck, ideally an F-250 or equivalent. People putting campers in the back of Tacomas and the like are playing with fire.