Played it on Tabletop Simulator as I mentioned on the server. Normal difficulty. I hadn’t played a board game in a long time so I had to reread the rules several times and it was hard to keep track of everything at first (but that’s just me). I wrote down every move. It's embarrassing, but after my playthrough I realized that I was adding the influence markers the wrong way (I was adding them to the result and not the die roll)… haha. I can’t really post my score because of that. But I had fun while playing. Megumu went dateless for six months while building wealth and Momoyo-maxxing, then leveled up the other relationships, and made some moves the last two months to buy more stocks and improve the final score.
I noticed that there are no ways to decrease Tsukasa’s relationship score. Is that something you plan to explore? I can imagine something like, if you don’t date her two months in a row, her relationship decreases because she requires more attention. Just an idea though, I couldn't tell if that would work for the harder difficulties. That aside, having to balance your relationships while picking your actions properly in order to earn more money or stocks was a good challenge.
Although not as convenient to play as other kinds of games (in terms of, having to use external tools or pen and paper), I value having more jam games in different formats like this one.