This sounds a bit like dodging the issue. I don't think it's the frequency of an act that makes it right or wrong.

I'm not really comfortable with the concept of receiving something I didn't work for or earn. But more importantly, I think playing the lottery, like Tyler said, does create attachment. You're telling yourself, 'If I won the lottery, I would be happier because...'. It's hard to resist the temptation every time they do a lottery pool at work but I refuse to give in because if I really want financial freedom I should instead focus on what I need to do in practical terms, on a daily basis, to make that happen. And I need to learn to be happy with what I have, not chase after things that are extremely unlikely to manifest in my life.

Why not? Buddhism may be relatively free of dogma but like any spiritual/ethical thought system, it necessary involves normative judgements. People choose Buddhism to begin with because they believe they should live a certain way...