It's hard. The very 1st time I played one of these was with one $10 entry(each entry was $10, and you could buy as many entries as you wanted to.) I made it to the top 20, and went out with some cheap horse called park the car(I'm serious..Belmont..very late May of 2004, or 2005.) Can't get back to the top 20. For me, it isn't about the number of entries. You just get really lucky, or you don't. I'd say that they get very frustrating to play. It's more about luck than handicapping.
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