Hi Jetsetter!
I really like your examples and stories. It is interesting to compare notes about exceptions made, accommodations that were made despite being against the rules, etc.
I was Prem Ex on UA with 98,400 miles so I decided to go over the top to become 1K.
Recently on my mileage run from BWI to the west coast back to BWI, I was travelling on a fare that is Tuesday/Wednesday, one day minimum stay, 7 day advance purchase, BWI-LAS via BWI-LAX-LAS-ORD-BWI. I upgraded by telling them I have two North American confirmed upgrades (which I do.)
I made the reservation to go to LAS Tuesday and come back Wednesday. Then I called back in 10 minutes and changed the return to Tuesday, LAS-ORD-BWI. I didn't want to go to ORD but I got an upgrade LAS-ORD-BWI. The phone person changed the ticket with no problem, informing me that there might be a $75 charge.
Travelling on the ticket I got what I consider royal treatment even though it was a $198 fare ($220 with taxes.) They never mentioned the $75, for instance.
When I got out of the plane at LA I got onto an earlier flight to LAS. In LAS, I called and got an upgraded itinerary LAS-DEN-BWI. They offered to fly me to IAD even though this is a much more expensive fare, but my car was at BWI so I needed to get to BWI.
I had the clear impression that I could have gotten off of the connection in LA, called and booked LAX-IAD direct if I had wanted to. I didn't try that but I was tempted. I had time and was enjoying my flights and getting a lot of work and thinking done, or I would have.
I'm sure others have similar experiences. Last July I travelled with my wife BWI-PHL-ROM-PHL using 2 systemwides on US instead of 4, because they had mistakenly informed me on the phone that I could upgrade a companion as well (and if you look at the wording on those certs you can see why there is the ambiguity.) I had to chat on the phone while at the ticket counter with US but they graciously gave in so I didn't have to use miles. I knew they would, too. I wasn't playing a game, I had confirmed this with them on the phone (obviously the person I had spoken to was mistaken) but they honored their word as I would expect. I am a US Gold Preferred as I mentioned, so only middle tier.
The times I don't get accommodated on UA is when they insist on collecting certs. I don't know if they've ever failed to collect them.
BTW, on the flight BWI-LAS routing, I gave them 500 mile certs in the club and they happily accepted them, so I still have my North American confirmed certs.