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Problem 1: The problem is the
while(repeat);
statement on line 120. Comment it out.
Problem 2:
while (want_to_play(money)) { /*...*/ }
Problem 3:
http://cplusplus.com/doc/tutorial/files/
Some other things:
-> Remove the call to srand on line 75. You should call srand only once in your program.
-> There's a lot of duplicate code inside your main loop. Consider putting it in a function.
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