I played this current version of the game and I have some thoughts.
I actually lost on my first play when I followed the girl off the bus and was robbed meaning I didn't have any money for rent. I got to the portfolio making but couldn't complete it because the game says you are too tired to workout at 23 energy. I assume this was intentional since the portfolio says its incomplete. I got to the point of where eve needs help, but I can't figure out what the game wants. I had the game crash in the hall outside your room quite a few times as well. And can you get rid of the necessity to buy toothpaste or soap? The number of times I ran out then had bad breath interrupt several scenes and was just plain annoying. You're already making us click brush teeth, I think we won't question how they're not running out of toothpaste or soap. Overall, there is quite a bit of new content and I'm looking forward to more.
I do wonder if a lot of the questions the game poses to you are necessary and I think a lot of the are connected to the depraved counter I suggested you get rid of. I think a lot of questions could be tied to the plot. As the character becomes used to the attention they receive and comfortable with their new gender, they would respond differently. Say, for example the character starts working at the coffee shop the first day they are a woman. They get a compliment and instead of the game asking how you wish to respond; the character has a negative reaction. The second time they get complimented they react neutrally then the third time they react neutrally leaning positively. The fourth time it becomes positive and the final time very positively. You could remove the randomness of what happens in what order and the character then moves on to bending over scene which has the negative where they immediately stand back up, neutral continue picking up then positive showing her panties. Then move onto getting groped and repeat negative/neutral/positive reaction order. This could only be done by making it, so the character has one job they do at the shop. The characters growth they will be a tutor and after some scenes there they do the glory hole handjob because they are embarrassed to be seen doing it. after getting some exp then unlocks giving the handy at the tutoring and ect.
These are my thoughts, and it would require getting rid of a lot of the randomness and the pseudo choices you give the player in favor of better characterization. You could get the character to bond with eve who could be the characters first time. Add the option to walk in the park with eve for the "bonding" and you know.