Well in windy conditions the squirrels tend to stay in their nests, wait untill a nice calm day then take your boy out. Also what time of the day are you hunting? Squirrels are most active early in the morning from sunrise till about noon, mid day it is still possible to see some but then from 3 pm till sunset is when they are really active. I've killed most of my squirrels about an hour and a half before sunset. I've had days where I didnt see any all day then limited out in the last 15 minutes of day light. If you can try to find some squirrel hunting videos, try to help your son understand that hunting is a skilled sport and not to be detered from a unsucessful hunt but to reflect on what you can do differently next time to make your hunt more sucessful. one of the biggest keys to hunting is alot of scouting learn the area and the times of day the animals are most active books and videos can help in aquiring techniques, you cant just go in the woods expecting to kill your quarry you have to understand them first, even squirrel.