I almost never bet two to win, but I don't necessarily disagree with the practice of doing it. If the price is right, bet them. The Sartain guys were famous for dutching win bets and created a whole movement of play that did just that by winning an extremely high percentage of races. You would really have to hit big percentages to cover the lost ticket.
The example of boxing and wheeling exotics is a good analogy. If the payout is right, you can absorb the cost of losing tickets and still come out ahead.
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Do I think Charity can win? Well, I am walking around in yesterday's suit.
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