I'm the mechanical mentor on the team that the original poster is the electrical mentor on....
I think we mostly have problems, because we have several different students working on the wiring, and some of them know about how to strip the wire to the proper length, how to find the correct terminal for the application (wire size, ring size, etc), and how to properly crimp. But not all of the students know this stuff, and we mentors don't always catch it when mistakes are made.
All this talk of adjusting ratcheting crimp tools properly makes me think this discussion has gone way over our heads here in southeast Arizona
btw I have a good crimp tool, and I don't have any trouble with using it to crimp insulated terminals on wires on cars and stuff at home...but building robots with students is a whole different challenge!