As a borderline Gen Xer, I grew up on Oregon Trail, so you had me at hello. I realize you ran out of time and couldn't do everything you wanted with this, but the amount of work already put in (in three weeks!) is wildly impressive. Could definitely tell that the township visits and the weapons at the starting point were meant to be something more. I still had a good time with this though! The only thing missing was someone dying of dysentary. lol
In terms of feedback, I did feel like the events fired pretty often, but the trail was short, so I would imagine in a full game, they would be spread out more. I'd also changing the idle stance of the people in the cabin away from the fighting stance. That was hilarious, but didn't fit.
Overall, for what you were able to accomplish, great job!