Everyone who says bet with your head and not your heart is exactly right.
I considered one time about betting against my beloved Penguins. We were flying up to Detroit for game 7 of the 2009 Stanley Cup Finals.
I was going to bet enough to cover the plane tickets, room and cost of the tickets. That way, if the Pens lost I would at least not pay for the trip and if they won I really wouldn't care.
I couldn't bring myself to do it and decided I was all in. It was either going to be a very memorable trip or the longest plane ride home of my life.
We all lived happily ever after......