Q: "A man in a blue hat is fixing the gears on his bike" Does this mean that "A male is making repairs to a used bike he just bought."?
A: it is not possible to tell

Q: "A man wearing a black shirt is outside walking with a shopping cart." Does this mean that "A man is wearing a black shirt outside."?
A: yes

Q: "A police officer is riding his horse down a city street during the day." Does this mean that "The police officer is brushing his horse in the stall."?
A: no

Q: "A family looking out a window watching crowds of people holding umbrellas in the daylight." Does this mean that "Its extremely sunny."?
A:
yes