Q: "A back view of a man driving a tractor and signaling with two children as passengers at the back." Does this mean that "The kids drive the tractor, while the man sits on the back of the tractor."?
A: no

Q: "A woman wearing a Little Mermaid costume stands in front of a bright red phone booth." Does this mean that "woman on halloween"?
A: it is not possible to tell

Q: "A man with a headset is rummaging through hay." Does this mean that "There is a person with a headset."?
A: yes

Q: "A man sits on an ornately designed stone bench, his legs crossed, looking at his smartphone." Does this mean that "The man is waiting for a phone call."?
A:
it is not possible to tell