Not sure what you expected. After the second one it should have been clear. As power goes up, the tolerances drop when it comes to what you can and can't do and how forgiving it'll be if you miss a shift, drop it at the wrong time, etc. I'm not saying it's your fault specifically, but it's like walking on egg shells when your power levels get higher and higher. If you're good (and lucky) stock might get you by for a while but you'll save more time/money/effort if you do it once and do it right. I hear you drive hard (especially after your dyno!) so now is the time to strengthen what needs it. I'm the same way with beating on my car which is why even on stock turbos, I went to the racing tranny.
Talk with Greg about it some more. You'll either find the problem or figure out a way to bury it =)