The current roadmap to the next version sounds like fun. I agree, I think it is a good idea to have all (or at least many) of the stories link up or feed into each other - it is all a big conspiracy against the player!
I wonder if it should be impossible to escape from cages. At the moment it is possible to do so and that can break the game logic when your captor announces they will release you even though you're already out...
At present when you try to escape some bondage predicament you can just immediately try over and over until you succeed. Maybe limit how often you can make those attempts - it will force you to wear those accessories for a while during the day and make your life much more complicated. The alternative of making the escape mini-games harder to succeed on might lead to frustration.
It might be that it is too easy to make enough money to keep you out of trouble, at least at first. Some additional money sinks to force you into the scenarios might be fun. Raise prices? I realize making an economy that is real-world realistic is not what the game is about! Maybe limit some of the basic money-making tasks so that you can't do them too often - maybe you can clean Chloe's place only once a week, do a coffee shop shift once every two days or something.
Maybe there is a cost for taking the taxi and if you don't have the fare you go into debt to the driver and you might need to work it off in, ahem, other ways (they visit you in your apartment and try out some of those toys on you that are lying around?). Or if the debt gets high enough you get another visit from the police. If you get stuck in town overnight because you don't have taxi fare and need to sleep on a bench or in the alleyway you might also get picked up by our friendly policewoman...
Of course another way to get the player into trouble is to force certain actions such as is done for peeking at Chloe's writings. A very nice touch as it simulates the player's inability to resist her compulsions (in this case, her curiosity).
I've only gone into the game a short way so far and I was really surprised when I was put in jail - I was not really expecting that and it was a wonderful moment. When released I was dumped into town nude but I still had all of my inventory. I thought the police said something about keeping my clothes as "evidence" but they did not seem to do that.
One thing I noticed is that the player needs to take a taxi home whereas Chloe's apartment is downtown. However, when rent is due she shows up at your apartment saying that she heard the landlord coming up the stairs - which suggests the two apartments are in the same building, and not a taxi-drive apart.
Lots of ideas could be thrown out there but you have to stick to your roadmap - these are just wish-list items and random ideas that you can happily ignore if you like!
Anyway, keep up the great work! This is such a cute game. Have you considered using Discord to help manage your feedback?