Your thinking is in the right direction. I would make all of the cuts, leaving enough material for a finish pass. Then do the measuring, and if OK, then press go and finish the part. I'm guessing that the worst case is the tool would wear or break and would not remove enough material rather than taking too much. The problem might be that the tool did break or had excessive wear and the insert need to be replaced, now you have to reset the tool and hope that you got it right.