I made it to day 80, 101 and 120 on separate runs, here are my thoughts.
sexual progression. It takes forever to get the pilot to any significant level of change in clothing. With stations seemingly only ever having 4 officers to gain quests from, and some of those officers never asking her to wear less clothes, it can feel futile to play. Especially with my 120 day run, I had to hard focus on getting people to lvl 2 then working on majors and colonels to get enough money to last that long, which made it impossible to try and get her to minimum clothing on any station. the best i've been able to do is 5 clothing changes, and even then it doesn't feel that substantial. It might feel better if every level gave 2 clothing changes or an "event" but even then im not sure. And with it taking a total of 1/3/6/10 quests to gain progression with an officer, if you have a "useless" officer or if they ask for date/ kiss/ grope, it feels like a curse (for the player) as opposed to the progression it should feel like. I think my real problem with it is. is the game supposed to be a survive as long as you can game, or a porn game. At least currently it feels like you have to play the game one way or the other, and just never be satisfied with your result. Personally I would prefer this to be a porn game with a bit of a challenge. Not a challenge game with a bit of porn. But that might just be me.
"useless" officers. There are officers that not only give you less money for doing their quests, but they also never ask for the pilot to do any favors or change clothing. this feels like a weird trap to put in. Maybe if they were changed to give more money but never ask for favors it would feel better. But again this takes away from why we're (i'm) playing the game, to see the pilot (presumably) turned into a slut.
I think you should modify the introduction system so that the player knows who is subordinate to who from the beginning and can only interact with majors, colonels and the general after they have enough levels with their subordinates to gain quests from them. seems a little odd that a random delivery pilot can walk up to the the general on day 1 and bug them for a job.
Too many stations. for the current gameplay loop i think 10 station is just a bit too much, especially when you have stations with only 4 quest givers on them. If you make the game a bit easier I think 10 stations will be fine but for now i think 6-8 stations all with 5-6 officers will feel better to play.
Dates. I only made it to the lvl 1 dates and im not sure if there are higher tiers of it in the game yet, but i think dates should A) give a monetary bonus B)give a moral bonus. I know these things are supposed to be negative but the dates in game seem pretty alright? It seems like a nice/fine evening so a couple (-2-5) moral points would be nice and maybe a tip if the pilot does something extra ;)
missing a payment. I think you should have a relationship value with the loan shark that you can increase by doing favors, I.E. he tells you to do a quest for a specific officer at the beginning of the week, contraband deliveries (high relationship gain, low income gain) or more personal favors. and when you miss a payment while having high enough relationship value he will pay off that weeks payment without counting it towards the fail limit.
Moral. Moral is a bit rough in the early-mid game but by the end game you have enough moral gain from evening events that it doesn't matter. Maybe add an evening event where you can trade moral for money. would also help for squeezing out that last little bit of money you need sometimes.
Moral loss from doing deliveries. currently it seems random how much moral you lose from from doing a quest. I think this should be changed to the further away the delivery location is, the more moral you lose. Or just make the moral loss from the mission more apparent when accepting it.
difficulty. Currently this game is very hard. If it was a roguelike were you gain long term progression at the end of a run i could understand it. but as it stands it just feels difficult for difficulties sake.
officer spread. It would be nice if you could limit stations to having no less than 3 captains on them, otherwise its really easy to miss out on quests.
also, Please make it so that they always give quests, I have had 4 days in row without being able to accept a quest. its honestly awful.
Sorry if i came across as very negative but i do really enjoy the game, but after my 3rd playthrough really trying to make it as far as i can and see as much of the pilot as i could, I feel a little defeated by the apparent futility of it. BUT i do look forward to seeing this game grow and expand and i can't wait for the next update!