It is given that there were 6 attempts in the game and all the five players got different number of dollars. The maximum number of attempts a single player could have rolled the slot machine has to be 2 (if one player rolled the slot machine in 3 attempts, then two players would end up with the same number of dollars).
Jack was the only player to get 2 attempts consecutively and he did not get the 1
st attempt. The number of maximum possible attempts by a player is 2, which means Jack got $10 in the first attempt, and in the second attempt he paid a penalty amount of $5, but from (iv), the player who rolled the slot machine in the last attempt won the game.
Jack couldn't be at 6
th.
Possible positions for Jack are: 2, 3, or 3, 4, or 4, 5, but there is change in sequence (from (ii)) at the beginning of the 4
th attempt and the 5
th attempt. So, Jack couldn't go at the 4
th and 5
th attempt.
Sequence[attempt number(name, amount)]: 1, 2(Jack, $10), 3(Jack, -$5), 4, 5, 6(xx, $10)
This means, the 1
st, 4
th and 5
th attempts didn't hit correctly and they would pay the penalty.
Sequence[attempt number(name, amount)]: 1(xx, -$5), 2(Jack, $10), 3(Jack, -$5), 4(xx, -$5), 5(xx, -$5), 6(xx, $10)
There has to be another person who rolled the slot machine in 2 attempts. This person also could not have rolled the slot machine in the 5
th and 6
th attempts.
Hence, he must have rolled the slot machine in the 1
st and 5
th attempts.
From (ii), this person has to be Luke because only by getting the 5
th attempt could Luke move to front of Jack.
Sequence[attempt number(name, amount)]: 1(Luke, -$5), 2(Jack, $10), 3(Jack, -$5), 4(xx, -$5), 5(Luke, -$5), 6(xx, $10)
Will must have rolled the slot machine in one attempt without hitting the jackpot and Franklin must have rolled the slot machine in one attempt and hit the jackpot.
Sequence[attempt number(name, amount)]:
1(Luke, -$5), 2(Jack, $10), 3(Jack, -$5), 4(Will, -$5), 5(Luke, -$5), 6(Franklin, $10)
OR
1(Luke, -$5), 2(Jack, -$5), 3(Jack, $10), 4(Will, -$5), 5(Luke, -$5), 6(Franklin, $10)

Thus, we can see that only 2nd or 3rd attempt and the last attempt hit the jackpot.
Since the question asks for a 'definite' hit, the answer is 6th attempt.