I also was able to get the wipe out with 50% stepover. (I have some basic settings that I use and most likely this is why I did not see this the first time) It does seems that the % of cut has an effect on the output and I would also call it a bug. I think I will report it to tech.
Also I would not say that any software crashing should be considered normal. Crashing is caused by the software doing something that can't be done in the way it was programmed. This is why a programmer adds error checks and yes "User error messages" to tell you not to do that. Or limits added in the code to prevent it.
Since Bobcad is still working on adding features and operations I give them a little understanding. But I would think telling someone that it is normal would be the wrong thing to say. Maybe the person you talked with is getting numb to the whole testing procedure
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As for not being able to simulate I am not sure why. My Predator works good. I am not using subs though and maybe that has an effect. try turning off the subs to see if it simulates then. If not then I would guess soemthing wrong with Predator or it needs updated to the latest release.
BTW: My little triangle works just fine. Do you have any cutter comp? When roughing I do not use comp but let the path take care of it. This may be a post issue and not a software one. Maybe but maybe not.