I'll take a stab, but the OP has to promise not to be offended.....
I'll try to keep the typing to a minimum since it's almost time to go home
The DPE did not allow the applicant to demonstrate that he knew and could interpret airworthiness with a records inspection. A point of style is that the DPE did not allow the applicant to be PIC when he suggested another altitude without an explanation from the applicant. He also subverted his authority as PIC by telling him to 'consider me briefed'. This is actually a regulations bust on both.
If I were a DPE, I may have strongly considered busting the applicant for questionable decision making for flying in winds beyond his comfort level. I find it difficult to accept that his CFI allowed him to fly 25G30 conditions.
During the XC portion, the DPE needed to let the applicant get to the 1st checkpoint. IIRC 2 are required. Class C operations were a mess. The DPE created a distraction that COULD have resulted in safety issues.
The DPE also seemed to show a prejudicial attitude, in terms of overconfidence in the CFI and/or applicant. That could show that his mind was already made up prior to the checkride.
I also did not think it was proper demonstration of engine out procedures for the DPE to designate a location to land. The applicant is PIC and perhaps should have suggested an assertion of authority. It's possible the DPE wanted to know if he had it in him. There was no indication that command presence was in this applicant (sorry, no offense - just my impression).
Then the paperwork was questionable. The applicant was failed for a specific task, but the documentation says otherwise.
In less than 400 words...
OMG I am going to go cry!!! Nah, it's all good.
So anyway, I believe you are correct on most points, but let me reply.
The airworthiness of the aircraft was puzzling to me. I spent about an hour going through inspections, ADs, and all, but DPE was there, saw me do it. Still, it's not an excuse not to ask me. I could be simply making a smart face and pointlessly flipping through pages.
The "Consider me briefed" comment surprised me too. I had passengers with me during my dual, and I briefed them myself. Even after he said it, I asked him "So, your belts are fastened, and you know how to open the aircraft doors?"
For the wind, he told me, and I quote "Winds are a bit strong today, but I believe you will do just fine", and at the point, I had a case of "get-there-itis", thinking that it's blowing straight down the runway at my home field. So yes, definitely a lapse of judgement there on my part.
Also, agreed on XC. I deviated from my original plan to avoid airspace, but quickly got back to the route, stated the timer. I guess that was enough for the DPE. Still does not explain not going to at least 1st checkpoint.
How's Class C a mess? Yes, I forgot to get ATIS, but approach asked me to return with ATIS. Did that, and all was ok. There was a bit of a miscommunication/misunderstanding with DPE who originally wanted me to park, get clearance and go up again. When I touched down and told the tower my intentions of going to a GA ramp, this is when DPE gave me his WTF face and told me not to do it. Other than ATIS, I believe my class C work was good. If you see problems there, please let me know, I am curious as to what could've been done differently.
I believe for engine out, he selected the field mostly because of the area. And at the point, I did not want to tell the guy who has "keys to the plane" that "No, I will land here, not there". Where that part took place, you could land ANYWHERE. Lots of open fields, bunch of rarely used roads, I could literally point the plane to any point in the ground and land successfully. I guess he wanted to simulate something other than that. When I saw that I will have difficulty making the field that he pointed out, I told him that I can simply land at any other place here. And yes, PTS does say that applicant needs to select the field.
For paperwork, there are 3 things listed.
Emergency Procedures - He wants to see me do it again. He didn't tell I busted on it, just wants to see it.
Ground reference maneuvers - Busted part.
Takeoffs and landings - Was my choice not to do it, because wind started to shift a little bit