-I personally think it's a bit tedious that every time you enter a room from another room (ex: ken's house: Samantha's room into main room) you have every npc ask you what's up and you having to press the "bye" option so you can get out (even though you already talked with the npc). I'd say trying to place them in the background as a click-able image or something, like how you can see Anna in the bathroom.
-Then I think you should focus one of these updates on purely exploring and expanding the Starmaker page. Instead of 6 main upgrades and that's it, you have the option to upgrade certain things. Ex: Ads; you can start off with some non-lewd ads and then as you progress the story Anna let's you 'change'(upgrade) into medium lewd and then into straight up lewd ads. This can also allow for an ad-posing event where she poses for the ads. Then you could also have some temporary upgrades like "front page for 1 day/1 week" type stuff that boosts your income for a day/week. For the merch you can have it start off with mugs, then hats, then shirts, etc.
I'd also suggest studio upgrades. Anna shouldn't buy the entire studio equipment off the bat, but more like you can upgrade it over time. better lights, props, background sets, etc.
-Another thing I think would make sense is that Anna going to the gym, shouldn't just be for the sharing route with the futanari but you could also get some photos of her in sweat pants, lifting some weights, etc.
-Dynamic poses would also be nice, instead of the just the face changing they could also do something as cross their arms, point to something, lift an arm, slight body movement when talking to npc's that could make them come more alive (but this would be pretty hard I assume since you'd have to remake a bunch of sprites/make a bunch of variations).
-Streaming where Anna does a set of 3-4 random poses from a set of 15 or so and talks about some random stuff, not too sure about this one but it would mix well with the upgrades suggestion since you'd have to get better microphones, better computer/setup, etc.
I mainly love the game but right now you can basically buy all the upgrades relatively quick and be done with it as you watch the money increase. I'd love for the management aspect of the game to get expanded upon.