I'm sorry, but it's not making any sense to me. When purchasing anything, have you never once said "I'm not paying that, it's not worth it" or "I'd rather spend that money on something else of higher value to me" ie... how much you're willing to pay, is LESS than what the seller is asking?
Sure I've said those things. In fact I've just cancelled a cruise I've paid a deposit on as I've decided the money is better spent on a different trip. But if I want to take
that flight, I'll have to stump up something, and I look for the best value from the choices available.
Using an example - an airline is offering a flight at $10,000 cash, and you manage to get the same booking for $5,000 worth of points. You're trying to tell me that you will unequivocally say you're getting $5,000 (or is it $10,000) worth of value?
No. I'm saying by using purchased points on the flight I want to take, I'm saving $5000 over what I'd have to pay otherwise.
Where is your intrinsic valuing model, if you're just naively using the values set by the airline? Do you honestly believe in a room full of people every single one of them will agree that you just got $5k-$10k worth of value?
DCF?

But seriously, I don't believe I've ever assigned my thoughts to 'a room full of people'

. You seem to be stuck on whether a particular flight is 'worth' what the airline asks. I'm arguing no matter what they are asking,
I want to take that flight and I look for the best value. Often using purchased points gets me on that flight for less money.
You've now spent $5,000. Were there not other things you could have spent that cash on? Could you have taken the same flight in economy, and spent the money on a nice hotel? Could you have changed dates for a cheaper flight, and put the savings to good use elsewhere?
Well, yes, but I want to take
that flight. Yes, I could have gone in economy, and I could have used points for that too.

I could change dates around, but I want to take
that flight.
One thing that is quite clear by now - you guys are an airline's dream customer
Because I fly a lot, possibly, but since I'm often flying for half the price they are asking, I doubt it.