Aterpster: going back to your discussion of the EMT plate:
Would I go straight-in in Case B? Yes, it would be "counter-productive" not to, even though technically not "legal." But, what if I were receiving a check ride from a disgruntled FAA inspector? Well, in that case I would query ATC, "Am I cleared for a straight-in IAP from over POM?" If the controller's response was ambiguous I would then advise him that I have to do a circuit in the HILPT.
In 1996 Wally Roberts wrote that the controller wouldn't be authorised to clear you for a straight in from POM, and if he or she did you should refuse the clearance.
http://www.terps.com/ifrr/nov96.pdf - is particularly interesting. It's a bit old now, but do you know if that's still the official position?
I have to say the situation is entirely different in Canada, where you can (with the cooperation of ATC) fly direct to any fix on the plate using the MSA and commence the approach from there.