This is the problem with using betting examples to illustrate trade sizing. Betting examples are easy to use precisely because they have fixed probabilities and fixed payoffs. In the real world of trading, there are no fixed probabilities and no fixed payoffs.
If I may propose looking at it in this way: Certainly this is not the case in an automated trading environment where the exit is either a stop at a predetermined risk level or a profit at a predetermined profit objective. Also,
over the long run, even a discretionary method that involves all sorts of variability - breakeven stops, trailing stops, scaling in, scaling out, etc. should yield you with a set of data that will determine an average win rate and an average payout
over the long run. Even in poker and blackjack, payouts vary from hand to hand as do the probabilities of winning or losing any particular hand (even using perfect basic strategy with counting, one will lose hands he "should" have won and will win hands he "should" have lost - just as each trade is independent from each one before and after, so too is each hand dealt - even a "high" count does not assure one will win each hand until the shoe is completely dealt). Each hand is, in a sense, like a discretionary trade.
If you look at the OP's example, the scenario he has proposed, based on just six trials, is an even money bet with a 50% probability of winning. In this case
there is no advantage, i.e. he has NO edge, and over the long run, (the
very long run) his equity should be unchanged minus transaction costs/vig. Over the
short run, however, such even money bets with a 50/50 probability will still experience some equity volatility (deviation, variance - what some identify using the word "randomness").
Given the assumptions of the OP's six trials,
he has no advantage, and
therefore he should not bet. Such is the folly of the Van Tharp 2% bet mantra: The optimal bet size is edge-dependent, and a "one size fits all" money management strategy may sell books and course, but it won't make you money except by accident. Without knowing one's edge, one cannot accurately figure out the proper money management protocol.