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just played through your game and really enjoyed it!
I really liked how keeping up with all things in life got more difficult the older you got, it felt quite authentic and the music was really good to set the mood as well!
The soundtrack reminded me of Firewatch quite a bit (if you played that).

I also got some good laughs out of it and I guess I lived quite the interesting live, a 2 times homeless professor with 3 kids and his wive, living in a small apartment but becoming a rockstar in the end at age 59.

Overall a simple but effective idea and I´m impressed at how you got so much into it for a rather short game jam.
I´d love a bit more consequences - maybe you get ill faster or your wive leaves you when you get homeless? But it´s obvious that you only have so much time during a jam so that´s no problem at all.

Did you "hardcode" all the choices or how did you control what appeared when and under what conditions?
I wanted to get into walking simulators/storytelling games (like Firewatch) soon, so I´d be quite interested on how you approached the problem of multiple story "branches" depending on the players choices and keeping control over it.