Do you seriously think ford put the same tune strategy in the F150? I'm lost with you asking why the horsepower is less on 87 than 91, because it has to pull timing.
The air leak could of been the big problem depending how long he drove like that. The 87 octane gives less safety margin than 91+ will, even with timing pulled, compression is still compression and if he got bad gas, combined with the K&N, leaning the air already and the leak, i wouldn't doubt the motor issue
I in no way think Ford used the same tune for both the truck an the mustang. But there share the same engine which is why Ford is able to use 87 on both f150 an mustang with no issues. You don't under stand how the new pcm works its change a lot compared to the old one. It detects the gas rating when it does that it then can chose what strategy to run an when running on 87 it detunes it self. When it runs 91 it then runs at its full performance. But it doesn't matter what rating it is because ford made it to run on either an does it safely. Now if he got bad gas it still wouldn't matter if its 87 or 91 it would of still caused an issue.