Reality wouldn't be mean to you on purpose.

Of course there would be worlds where something would have gone horribly wrong if you won the lottery. But there's no reason for you to expect that you'd wake up in one of those worlds because you won the lottery. The difference between your "horribly wrong" worlds (don't care about money/ inflation / no money) and wedrifid's (lost the lottery and became crippled) is that waking up in wedrifid's is caused by one's participation in the lottery.