Indeed, though it doesn't have to be a time loop, just a logical dependency. Your expected payoff is α[p^2+4(1-p)p] + (1-α)[p+4(1-p)]. Since you will make the same decision both times, the only coherent state is α=1/(p+1). Thus expected payoff is (8p-6p^2)/(p+1), whose maximum is at about p=0.53. What went wrong this time? Well, while this is what you should use to answer bets about your payoff (assuming such bets are offered independently at every intersection), it is not the quantity you should maximize: it double counts the path where you visit both X and Y, which involves two instances of the decision but pays off only once.