Yesterday while I was playing I got the third Astronaut Jack (bring Toasted Cannabis), failed it by the narrowest margin, and quit out of my game to try again. The quest hasn't shown up from several in-game days, and I'd like to ask a few questions about these quests.

1) If I'd just kept playing would I have gotten another chance to do the same quest?

2) Is there something I have to do to trigger the quest other than just play a certain time?

3) Did my save somehow record that I'd failed the quest even though it was a save before I'd gotten it? Will I need to start a whole new game if I want to try it again?

Edit: Just realized I've had the Hotline disabled this whole time. Still interested in Questions #1 and #2.