I work in Reservations so I see a lot of various comparasions between the fare and milege award cost. Usually, I try not to offer an opinion when someone is debating between using miles or cash. Since that is their choice based on their personal preference.
The worst I heard about was a woman who used 25k for a short flight out West. She could have bought the ticket for $81, yes, just 81 dollars. The agent did advise her it probably cost her more than $81 to accumulate 25k miles.