Thank you for the info.
1. I played the save you provided, and the maintenance check unlocks once the cafe is available. In your save, you would just have to sleep and then go to the town center in the morning. Then go to the cafe during the day and bar in the evening for the scenes there. The next day, the maintenance check will be available when Sonya is working. I'll update the quest description to state that the cafe is needed.
2. The new game after quitting can be a bit buggy since it's rarely used (mainly added for translators, so I missed the things from hitting "new game" from there). Restarting the program is probably better for the moment. For cheating money/stats, you can also use the built in cheats (listen on the first post). I'll take a look at it and see what's going wrong there with not resetting properly.
3. It should unlock once you go to the town center in the morning.
I've playtested the game multiple times from the start, as well as had other people playtest it, but there is of course always something that can be improved, especially in the beginning. Playing through the whole game without skipping takes a very long time at this point, so I can't really do it before each release unfortunately, but I take all reports seriously.
So I'm thankful for all information about potential bugs and such, especially since no matter how often I play the game myself, I won't be able to find all the bugs, since I probably subconsciously avoid a lot of things that could be trouble, as well as potential bad descriptions of quests (like in this case).