Your chance to pull ahead diminishes with each trial/decision. Your best chance to be ahead is to make just 1 bet and then quit. You have a 45% chance. The reason is because winning two decisions, 45% X 45% is just 20.25%. You have to win both bets to be ahead. Win one and lose one....you are just even.
Your chance to be ahead after 2 decisions is much less than if you make just one decision.
Your chance to be ahead after 3 decisions is much less than if you made just two decisions.
More decisions does not give you a better chance to be ahead. It gives you less of a chance because of the compound effects of negative expectation gambling.