I think chapters is a good idea, and it´s probably easier to work that way too. I´m all in for that.
As for the tasks... hmm not really sure, I´d need to give it a thought but maybe getting everything back in place? let me elaborate.
Kinda like that RE7 dlc called " Bedroom" where it's like an escape room but you need to get things back in place before you get caught.
So maybe Jesse does all the things that he needs during the night and at the end he needs to put everything back in place so no one notices that he´s onto something