Q: "Man sitting on milk crate plays guitar on sidewalk." Does this mean that "The man is sitting on a large milk crate."?
A: it is not possible to tell

Q: "Two people singing and playing guitars." Does this mean that "Two people are playing violins"?
A: no

Q: "A slightly overweight young man, with long black hair and a green sweatshirt, leans back in a chair holding a bottle to his chest." Does this mean that "The man is passed out from drinking beer."?
A: it is not possible to tell

Q: "A person with a construction vest is using a lawn tool to cut hedges off the top of a bush" Does this mean that "The person is doing lawn work."?
A:
yes