For general behavior, I normally am extremely cautious. But when something big for me comes around, I usually work up the courage to... rip the bandage off fast, jump in quickly into the freezing pool. That kind of thing, and just tell someone what I'm thinking. And then freak out in embarrassment almost immediately. Maybe 40% of the time I end up regretting blurting it out later. Usually, something about an idea I had that had me excited that in retrospect I as being rather naive about. But that is still less than half the time so not exactly a bad success rate for something that you'd think would be more of a 50/50 thing at its base.
As for the example here, I usually don't chance a better sale on something coming around. But I have chanced a sale happening sometime soon before on something that was not on sale. This year that happened twice. Both for games. One did happen, one didn't. I chanced that ESO crowns would go on sale in time to buy expiring crown shop items in time more cheaply like they did last time there were a lot of expiring items. It didn't happen, and I had to pay more to get them ('m too crazy not to get them). And then I chanced that The Sims 3 and its expansions would be included in the Steam summer sale, it wasn't always. And it was, and I got it for 75% off.
For gambling in games, I don't exactly like it. I prefer to go on my actual skill rather than random chance.
For actual real world gambling in the literal sense, I am too cynical about things ever going right for me to really ever try it on my own. I have scratched those lotto ticket scratch off things before though. But then, only ones a family member bought that they asked me to scratch because it was "good luck" to have someone else scratch it. Nonsense but I did it anyway. Only things we ever won was $1 here or there, sometimes rarely $5, usually a free sandwich or something, which I don't eat.
