has he actually cracked someones WEP or just connected to an open AP ?
make sure he understands changing the MAC on his USB NIC and maybe look at running privoxy to strip a fair bit of info out of his http requests
show him this page
http://www.usbwifi.orcon.net.nz/
maybe he needs to look up focal lengths as his setup does not look very optimal
buy him a little 2.4 GHz yagi with a pigtail to suit his usb antenna connection and a cheap camera tripod
d/load , burn and boot a backtrack iso , or if he has enough CPU and ram he can maybe run it in virtuabox