Looking at the IMSB nut it looks like a stock nut to me...meaning Porsche. With as much dirt and oil as you have I doubt a new bearing was installed. If it was done a long time ago and the bearing was ceramic it would have to be a LN bearing.
I do not think Jake ever offered a bearing with a nut like you have. He uses Torque nuts. You may want to asking him if he ever offered a nut option like the Porsche stock nut. If I had to bet I would guess the IMSB has never been changed and the clutch and fly wheel has never been off the car before. See attached http://lnengineering.com/media/catalog/product/cache/1/small_image/504x504/9df78eab33525d08d6e5fb8d27136e95/1/0/106-08.4.JPG
Not related to the oil leak but certainly a factor in avoiding a future disaster - check the free play on the DMF. There is a very specific procedure and measurement. It is often done incorrectly .Badly worn DMF= doom.Measure both 'rock' & 'rotational' play.
They normally last around 90k miles+/- https://www.youtube.com/watch?v=uLp6nlYMssA
Did you clean the RMS and IMSB areas before taking the picture? I 'd order a new RMS and release bearing as well. Was the car parked for a number of days before the 'event'?
I guess it all points to getting the IMS bearing replaced. I know there are a ton of threads on this topic. I'll start researching on replacement manufacturer and tooling to do the job. I'm working with my indy mechanic on this. He's never replaced one before so I may be looking at other options. I'd hate to put it all back together only to have it all removed to install the IMS bearing.
Thank you for all the feedback, it really helps me out, at least knowing what section to read in the manuals.
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