I think it sounds like a cool idea.... Everyone is likely going to be in the freeroll, but it's probably easier for people to pay that money as you go instead of coughing it all up at once, so this is a great way to accomplish that.
If you think about it though, this set-up actually HURTS the best players in your game and helps the weakest. Figure even the weakest is going to win at least ONCE, so everyone is going to be in the freeroll. If that's true, that means the person who won the most times will have contributed the most to the freeroll money. the guy who won the least (say, once) will have only contributed $10.
Interesting.
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