Being as I don't have enough dives to say I'd do anything more than 'CALL IT', let me approach this from the perspective of a military helicopter pilot and a similar type situation...
I'm the platoon leader for a platoon of OH-58D super scouts (this is prior to the day they actually ARMED us, so we are just flying recon computers)...
I'm also the training area manager, I keep the record of every hazard in the training area, every wire, every grave vineyard.
I'm sent 10 pilots of varying experience, but only 4 of them are NVG qualified, and I only have one instructor pilot (and SIP), he has never flown the training area. I am under PENTAGON orders to train all of them up to NVG standards in 10 days before deploying to Saudi prior to Desert Storm...
There is no way the SIP can accomplish this, and I am a PIC, with 300 hours of NVG time... do you fly?
Now to make this a little more like your scenario, our CG (commanding general) comes to me and tells me that the SIP will check me out for NVG ops first, if he finds me HIGHLY CAPABLE, he will authorize me to act as a limited time NVG trainer... my first two flights are with the SIP, one for his area orientation, one for my check out... I'm good boys and girls, I am authorized to train... from the LEFT seat... (big deal, trust me)
So, here is one of my new 'students', a long time CW3, good pilot, very cautious, but hates NVG flying... so much, he hasn't logged but the minimum in 5 years, and always flies with a instructor pilot, never at true PIC. Do you fly? (mind you, I'm not in my usual seat, I'm in the LEFT seat, he is in the RIGHT seat where I am used to getting my visual cues)...
To make it better, he clearly has issues getting his equipment set up, he hasn't worn a skull cap in years (reduces the added weight problems for the goggles), and he's very skittish...
We start with traffic patterns over the airfield, hovering and take off, no problems, but his approaches are way steep, and his hover OGE (out of ground effect) is pitiful, more than that, flying NOE just over the airfield and maintaining constant altitude is (consider this peak buoyancy of flying) is bad... do you take him into the training area with trees, wires, fences, and haystacks?
Well, let me tell you what happens with confident and relatively experienced pilots, we do things that probably we shouldn't in the name of God, country, and personal pride...
I took him out, I flew the route start to finish at 40 knots with him on the map following, then we went back and had him fly it, with me on the map... we avoided at least three tree strikes, he quite nearly put our skids into a bush, and I didn't let him do the power line under flight, because it was time to call it.
End of this story is that we should have called the flight, afterward, the SIP and I determined that he would need to fly with each pilot first, and assess which ones I could train...
So, in an effort to make this come together, I've learned over the years to be very cautious, and correct issues on the ground (out of the water) in advance, never take problems with you.. that's asking for trouble...