It would be good if the dev would play the whole game from start to end-of-content once or twice again to get a feeling how the pacing of the current game, the relationships, the transformation, money earning and spending, etc is.
The game has a lot of content for different tastes, but it is to a large degree grindy and repetitive. It takes ca 30-40 weekly cycles to reach end-of-content unless the player chooses an early ending.
The mob blackmail with weekly increasing costs adds almost nothing to the game since the player has to follow the mandatory main path of becoming gay/bisexual and work as waitress anyway. It's just a repetitive weekly event with crude numbers. I wonder if a different approach with just telling the player to pay a total of maybe 100,000 $ + 1% interest per week in self-determined rates would be more fun. This would also avoid the case where new players now fail to earn enough money in the first week and are removed from the game with a bad ending or would temporarely deal with the late game case where players accumulate like 50,000 $ extra cash and have no options to spend it. (Since the mc's income increases while he progresses in the game, there probably will always be situations where mc has too much money which cannot be spent.)
Replaying the game felt strange, especially Katie's story. She is eager from start to turn mc into her female clothed pet-waitress, slaps his butt, strips naked for him ... and then it takes like 100 days for them to have a single lewd scene when mc steals the key to his own chastity device and then she is removed from the game for about another 100 days (maybe to not have to have more lewd scenes with her yet) before she finally returns to have some scenes with mc as part of the latest/late game content.
Katie's demands on mc to increase cross-dressing are mostly reasoned by 3rd party ... It would be more plausible if there would be kind of a "sexy waitress" rating effecting the waitress-money and tips. Each cross-dress-stage like shaved legs, sexy underwear, stockings, high heels (!!! missing!!!), extras like boobs (natural or augmented), make up, etc would increase rating and earning step by step. Depending on feminity rating Katie could have a list of new talk options and mc could pick one per work event. This would avoid unusually crowded events like demanding 3 changes (makeup, nails, buttplug) in one turn.
Katie could actually also suggest the chastity cage for mc as a device to wear shorter, more sexy, mini skirts without a visible boner to get a higher rating. (And she could exploit the cage ...) (To connect with current content of "chastity key heist", the boss would somehow have to take the key from Katie.)
Olivia could coach mc to get a more feminine, sexy body shape by regular workout at the gym.
Katie and Susan are both studying at the university. There are a lot of gender and femdom themes in Ms Domina's class, so the three woman should actually have the option to team up against mc. It feels strange when Ms Domina talks about stuff like face sitting, pegging, etc and then it takes hundreds of days to finally get these themes in the scenes with Susan or Katie in the game.
Early scenes with Susan miss a lot of options. Once mc starts to act strange and crossdress, Susan could talk with Ms Domina for advice, eg when she may notice that mc wears her (Susan's) panties or a chastity cage or buttplug at date night, etc ...
Once mc no longer can satisfy Susan with his dick, she could ask Ms Domina for help and mc could try other means like using his hands, tongue, sex toys and watch porn with her instead of letting her go home to watch porn alone.
For a game of 30-40 weekly cycles the current policy of dating only one person feels wrong. There simply isn't enough content for any dateable character in the game yet for 30-40 weeks. Therefore it would be best to allow mc to befriend and date all the characters at will to have at least more content in a single playthrough. Susan felt to be the character with the most dating content, but her content is divided into separate routes like true love, threesome (with Todd), cuck story (Chad) and BBC (Oliver). Instead of locking the Susan relationship on one of the four paths, it would be better to allow the mc to switch from one path to another midgame to have more available content for the 30-40 dates, similar to the current cheat menu. (Actually not all of Susan's date events seemed available via cheat, especially those when mc dates Susan+Chad or Susan+Oliver seemed missing and only those when mc dates Chad or Oliver directly were available.)