Hey, I finally got around to playing this on a PC. It was a lot of fun! The sense of humor was great, I loved the descriptions of the cards and narration. The pixel art was really nice, as was the music and overall "feel" of the game. I wound up playing it a few times!
I enjoyed the main card mechanic, but since my hand was randomized each round, I feel like it was just sort of random whether or not I could meet the criteria. Maybe if I kept my cards between rounds and it just replaced the ones I played, I'd feel more agency over whether or not I succeed. I'd also have more of a reason to actually use the cards that don't have any value, like kleptomania or insomnia, just to get it out of my hand. Or to hold on to really good cards that are either overkill or only half apply to this scenario.
I had very few technical issues with the game. The main one was that when I tried to press "Again?" after a game, it would reset the game, but I wouldn't be able to click on any places to go, so I'd just be stuck until I quit and reopened the game. That was basically it. I also had a few layout issues (the "fullscreen" didn't cover my windows start bar, and the names of the different places were mostly covered by the pictures of the places), but I assume that's more of an issue on my side. I don't expect jam games to be formatted/tested for all screens.
Aside from that, it was very smooth sailing! And again, I really had a good time with this. Like I said, the game is very funny, and I went back multiple times just to make sure I got to see all the text. And I had a good time doing it. Great job!