I did it several times already, I did not even use the highest winning chance when I participated in a wagering contest.
Simply because I have tried using high winning chance but failed earlier because getting many losing bets.
Mathematically if we use high winning chance, then we need to have so many winning bets to recover 1 lose bet.
Obviously there is no guarantees that we will be able to wager more by using specific strategy as everything based on our luck.
It is just about preferences, every players has their own strategy and has their own luck.
So which is better between playing with low win chance or high win chance according your experience while joined on wagering contest? It must be playing on high win chance, isn't it?
Sure you can lose multiple times in a row while playing on high win chance, but the chance of that happened is much lower than lossing streak while you playing on 49.95% win chance or 2x payout, which can bring you more than 18 losses streaks.
People who using 2x payout is only aiming for profit because they are high roller (but sometimes they are the winner of wagering contest too)