IFR Filing ?

Knowing the instructor in question, it's probably just one of his many "-isms" that no one knows where he got it from but he certainly won't listen to you no matter what evidence you present to the contrary.
 
I had an incident with lost coms on an IFR plan coming back into the DC SFRA (cleared all the way to destination airport). As soon as I hit an area I could descend and land VFR, I did which was outside the SFRA. I squawked the lost comm code and called Potomac as soon as I could. They were well aware of my situation and were hoping I would call them. A lot of lessons were learned that flight, but we did have a positive outcome.
 
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(2) even as a planning exercise it makes no sense since choosing an IAF in advance assumes the winds won't change, not exactly a given in real weather.

You pick your preference and go with it.

Last trip, the captain would always do this when putting in the flight plan. It was driving me nuts because it was making it a PITA to verify the length of the flight plan in the FMS vs what we had on paper. I just rolled with it though, and when it would change, "hey, would you get that for me. Looks like you were wrong, again." It was a comment made in jest, so I got to poke fun at him which makes trips fun when we can rip on each other like that.

But to your point. When doing it IFR as a young buck, I used to file from a fix on an airway (VOR/intersection/whatever) to the airport. If you've lost comms, chances are, you've lost a lot more than just the ability to talk to ATC.
 
Knowing the instructor in question, it's probably just one of his many "-isms" that no one knows where he got it from but he certainly won't listen to you no matter what evidence you present to the contrary.
I've have never flown with this instructor, but we've all flown with "that guy". It's amazing how many "professional flight instructors" persist in teaching incorrect information despite what is clearly printed in the FAR or AIM for no other reason than that's the way they've always been doing it.

The military is guilty of this as well. Most of their system is great but it is not always 100% lined up with civilian operations.
 
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