Well there is something in there that it doesn't like. I did a second job which is to just machine two small bores with the same tool setup and that generated no problem. Got to watch it get simulated which is pretty exciting. It doesn't tell me that the shoulder of the mill will crash (the pocket is deeper than the depth of cut and the tool I used to test has a shoulder) so I will have to keep an eye out for crashing unless there is a button to have it check for that.
I might need to figure out how to change the UCS a touch more in the CAM tab. My Z is fine, but my X and Y are flipped. Might not matter on this part, but will run out of travel on another part.
Also, I figured out why I couldn't select the tool holder I had created. This is from a page or two ago. Turns out that you create the holder, but then go into a tool profile and pick which holder you want. I was almost there, now it looks just right.
Progress is good, just need to tackle this next bigger bite.
EDIT: I think I got it, but something else is off. I was changing things one at a time and when I changed it so that it would allow stepover cusps, it auto-generated the toolpath. The new problem is that the Z never goes below zero.