So I also gave a different answer here (FIRE now) than in the gambling scenario (don't gamble) :)
I don't think they're completely equivalent. To take the gamble the following conditions must be true, as you outlined in the poll:
- The amount of money you have now is not sufficient
- The extra money you would have next year is completely irrelevant
- There is no way to stop working halfway in the year, or to work part-time
I can't imagine all of these conditions being so rigid that I'd take the gamble. If there is any doubt about the assumptions, it will also make it much harder to not beat yourself up over losing it, and losing $50k in one gamble takes a lot of mental strength to just wave away as "it was the right decision so I'm fine with it".