Have a look at jaipur ILS 27, theres a box that says that ATC may allow a aircraft to join the arc from any radial which basically means if you arrive from a short cut and not on the airway radial you could join the arc procedure, in that case you would not be flying over a IAF. I think thats what your check pilot meant. The same is mentioned in VABP/VILK too. In case of an emergency fly the IAF/IF/FAF sequence when things go wrong SA goes out of teh Captains window first.
Not permitted by the FAA under US TERPs. We finally do have, though, a few US ARC initial segments with multiple IAFs. (HQM and HLN come to mind).