Give the guy a break; he is likely a consultant of some kind looking to install a monitoring well or boring on the City ROW (Your planting/parking strip). Experienced folks mark a box but newbies might make a blob where they want the well to be. By law he has to use white paint.
You might want to contact the City and see if a Street Use permit has been filed. If they are gonna drill it will be near next Wednesday or so because “One Call” needs two working days to respond, and Friday doesn’t count.