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It's not that difficult. All you have to do is think that there's a little child behind the doors that places the $5. You can easily trick the child in most of times because the child doesn't have the AI to always trick you (it's just java code after all). Just always pick the last winning door and remember which doors where "X" in the 2-3 previous times. Normally, you'll find the 5$ in the most "X" marked door of the 2-3 previous games. Once in a while you may really not know which door is because the chances are 50% even with that method, so it's plain luck. My english isn't my native language, therefore it's not easy to make you understand how to understand what I've understood for understanding this game. :p

By the way my score was 23/27, which under circumstances it gets better.