Let me start this by saying that I don't like being laughed at by people younger than me. That group probably includes 85% of you, so show some respect and at least laugh behind my back. So, I rode Harleys back when people didn't think running motorcycles off the road was a sport. My father-in-law, rode all his life till he got killed on his. We both bought our scoots used. Once, while I owned one and once while he did, we had Harleys where the engines locked u. Both times it turned out that the two different geniuses who had done the rebuilds put the cams in backwards. I know that sounds unbelievable but some of them will run like this until you press them too hard.
Another and more probable issue is gas. Most injected Harleys are rated for high octane gas. 87 octane can and usually will make them ping which is mechanical speak for "I'm about to really crap on your day", followed shortly after by a nice lunch of fried piston. (Bring you own catsup)
IMO, if this kid is stupid (yes, I said stupid) enough to fry the engine twice, it is God's way of saying "maybe you should ride a nice G-Body and leave the two wheeled stuff to the grown-ups."
Just a thought.