Sprint HTC Hero :: Won't Root - Racking Brain

My brother was scared to root his, but now after 3 months, he's finally secure in the thought that it won't kill his phone, so he decided to root. He also has a Hero, the exact same phone as mine. The only problem is, his won't root. Initially he tried doing it via the latest version of Kitchen, with the single click root. It didn't work, so I tried it just to make sure he was doing everything right. What the results are, is after the auto root, upon reboot, while holding the home key, it won't boot to the recovery screen. The screen goes black with only the triangle and exclamation point with the little phone pic next to it. The battery has to be pulled to restart it. Everything boots up fine after the battery pull, and it runs as though root was never attempted.

Well, last night I had to update the recovery shell on mine to 1.6.2, so I grabbed his phone and figured I'd try doing everything manually through a DOS window and adb. I did mine first, and had no problems at all. Reflashed and all is well. When I manually did his, it gave the congrats, enjoy the shell message, but still won't boot to the recovery screen. It still boots to the triangle and exclamation point pic. I did his EXACTLY the same as mine.