For the sake of discussion, lets say oiling is good.
I can't imagine a single pipe and reeds pushing the motor over the edge to needing race fuel, but maybe if the ignition timing is over advanced? Just because a motor has a deto sensor doesn't mean deto can't kill it. Deto has to happen to be detected, so while each occurrence on its own may not cause much damage, repeated cycle of: [deto, detecting of deto, and the resulting timing retardation the PCM initiates to save the motor] will add up and could eventually be beating out the rod pin bearings.
My PTO side rod bearing was flattened last spring. Throughout last season, maybe every 3rd ride, I'd see the deto sensor flash at me at some point during the day. I kept riding it, didn't really change anything except some jetting. This was with SLP race twins, but otherwise stock motor, 29* BTDC timing at 8-12'k. It was difficult to see, but there were little tiny indentations around the edge of that PTO piston, further confirming the deto.
Take a very close look at the pistons, especially around the perimeter, and look for small pits/indents. May need a magnifying lens if your eyes aren't as sharp as they once were. If you see these indents on both you may have had deto in both cylinders and its just chance which once breaks first.
As stated, check oiling. Check timing. Could go with a better designed head than stock, or a gallon/two of 110 per tank.
Disclaimer!: Just so you're aware, I'm just a guy that reads too much, not a real expert.
Edit: Just saw your buddies sled is an 02, so not det sensor. Look real close at the pistons.