So the JD pic is someone mowing a several huge properties (like industrial parks and home depots) that are out of state/out of the area, so they travel a silly long distance (hours) to mow properties in the area.
The truck drops off a few mowers in more than one location , then they either use local guys who meet the equipment there, or they bring the guys with them (a lot of travel time to pay for tho)
TYPICALLY the foreman drives the equipment back and forth from HQ, the labor are local talent.
This was a "back in the day" brickman/valley crest behavior
The SCAG PIC? Ive never seen that TBH... three wheel rider STHMS? how old is the pic/when was it taken.