Computing toolpath error

I am getting the same vague error others in the past have.
I've noted it is said that we need to have all green checks. Question: do all portions in orange need to be green, and then implicitly the blue will all be green?
As a note, I've made all checks green and it still will not compute. So I assume there is an actual computation issue. But how do I know what?
I think it would be very good to have more context with why a toolpath computing error.
1) setup issue, if so you shouldn't be able to compute at all. 
2) actual computation issue, tool size, stepover issue, etc