I was being stingy with the support and one of them promptly tore off... tried to salvage the print with gaffers tape, but then when to double check my print and found one other issue with it. Redid the slicing with a solid block of support covering all four holes and the rest of the overhang just to be save :)
Forgot to change the number of top layers on one of the processes, hence the little holes in the part. I guess I need to talk to Simplify3D about some ideas I have on how to prevent that.
At this point I was a bit in a hurry. 2 days till deadline and still plenty to print. This isn't as nice quality as I would have liked, BUT, being on time was more important than it being absolutely perfect. I can always reprint it with what I've learned in the process