let me try.
1. The effect of vol goes up could be deemed as stock price moves closer to strike. So for vanilla call & put, gamma increases when vol goes up; while for vanilla digital, it depends.
2. I would assume that you are risk neutal. Then for the 1st round, if you see a number less than 5, you should choose to continue because its expected value is 161/36; for the 2nd round, if you see a number less than 4, you should choose to continue because its expected value is 3.5