Troop, I will not spend too much time on the multiple quenching, since it is an excellent way to get U.C.O.K's thread hijacked when the true believers get agitated about the underlying factors. But if the soak times are there and the temperatures are dead on there are two factors left that I immediately think of - loss of carbon in repeated heating, or lowered hardenability due to grain reduction, which really will not be a factor in O-1. I am not at all surprised by you distortion issues, I have chased a twist pattern O1/L6 hunter right around in a circle by repeated quenching without any stress relieving operations in between (just playing, not making one to sell.)
O1 has a few more elements to it's chemistry than many of the steels we smiths work with, it really isn't very tolerant of "creative" heat treating, this is one of the reasons I am hesitant to recommend it as a beginner steel.