As Dylan mentioned, without the file it's hard to be of too much help, but with that much overlap, I'd take a close look at your clearances, side tilt, and lead angle. By default, the minimum lead is 0, but sometimes you have to lead a bit as the tool tilts to get under that overlap from the main blade. Try something crazy like allowing -45 to 45 lead angle and 90° of side tilt and see if that solves it. If it doesn't, it's probably your clearance amounts. If the lead/lag or side tilt solves it, then dial it back down to see what it needs. Remember that the problem with roughing is that you're leaving stock on the blades, so even though it looks like the tool "Should" fit through the slot, the slot is smaller by X on all edges from the stock left on the blades.

I have a lot of experience with macros and probes. What I lack is understanding what I need to do to adjust the probe to set itself to a bored hole, all the ring is for is reference and not inspection, thats why they make dial bores. I am just looking to do simple pickups for G54. Right now its for a horizontal Mitsui 15M control and right now the guys are running a complex macro that does not work. We can write to #100 and #500 variables. The machine does get ball bar tested and you are spot on about not using them like cmms, thats what cmms are for. Thanks you again.