Pixel scaling is way off between assets. I would highly recommend keeping a uniform pixel scale for all in-world elements and a uniform pixel scale for all UI elements. Even though you made all art assets for the Jam they look like a mash-up of random assets due to the mix of pixel scales.
The black boxes with text at the beginning of the game made me understand what to do instantly and got me into playing very fast.
Fun and interesting gameplay. My main concern is the difficulty scaling. In the middle of the game, I felt like I was very close to winning with little to no awkward/weird meter. That got fixed in the later game but I feel when I got a lot of bad results and my awkward meter caught up with the 'good' meter.
The only thing that confused me was the dice that gave me more dice. I think it could be clarified a bit more what it is by having a similar black box around it with text that explains it the first time one of them appears.