What's the highest possible cash value? I would say an upgrade on a long-haul INTL flight in J for $6K when you paid $1K for Y is about as good as it gets. Say I buy an eligible fare class and upgrade for 40 PP, that would be $5000/40 = $125 per point. That is on the extreme upper end. On the lower end, Kacee has it right and I routinely see those offers all the time.