my guess is if he had a non-broadcasting ssid, he would know it because that is not the default for any vendor i know. same with mac filtering. and yes, with heavy traffic i have gotten a wep key in under 10 minutes. however, due to a totally different encryption scheme, wpa is much (read: really really hard) to crack in a short period of time (read: less than a day). no encryption is perfect, but any is better than none.
my wireless wardriving efforts have all been on linux, but the principles of setup are the same. if the default os wireless is not working, the best way to see if your card is working is to get a 3rd party wireless option. If kismac is anything like kismet, give it a whirl. It will pick up all broadcasting and non-broadcasting in range no matter what the settings are. If that picks up nothing or doesn't recognize a card, you can go from there.
Also, have your friend come over or anyone with a wireless card and make sure that your router is up at the time you try to connect, just to be sure.