Well, I didn't set out to discourage... My point was that this game can well be dissected and analyzed, only that perhaps a less laborious approach would make it possible to reach the end
Let me see if I can't compile a list of Lewdness increases in the game. That in itself should give the reader a rough overview of what the game contains and how to gain (or avoid) Lewdness.
Then obviously more context would be welcome in those instances where the "if then else" logic is particularly involved; where it isn't obvious how to reach a certain spot.
An example:
Early in the game Ben asks you to come to school next day wearing something more daring. The key information to give a reader is that the important thing is to wear something with a higher Lewdness score than you have ever done. That is - if you play the game like many people do and always try to max out your Lewdness, you can't reach the goal of impressing Ben.
You specifically need to voluntarily keep dressing modestly so that you can still "break your record" on the day of Ben's judgement.
Not taking advantage of the Lewdness increases you have already gained. If you have already maxxed out your Lewdness, there is simply no space to wear something extra daring.
This is what the game keeps track of as max_slut as opposed to the slutty (Lewdness) score itself. And it is slightly counter-intuitive, especially for a p0rn game. (I'm not sure but I think this max_slut score is latter dropped and plays no role)
My point is that even a great flowchart (this you do cover in the walkthrough since it's so early) fails to tell the player what he needs to do. Or not do. That's why I'm suggesting maybe flowcharting this game is a lot of work for not so much payout. I'm simply saying another way of presenting the game logic might be more effective in conveying the essentials - what the player actually cares about: what to do or not to do, to reach a given outcome.
If you were to give this another stab that would be excellent