I've spent more time than I care to admit digging through the code and learning just how skilled Tristim and Starbuck are when it comes to coding.
AdventAnyx brought up a few great points that I'd like to address in detail.
There are currently two types of tooltips within the game: one tied to the character sheet (obedience, love, sluttiness hints), and another tied to the world map in the bottom left hand corner in the form of a question mark. The character sheet hints are initialized in the character's "<char>_definition_ren.py" that imports a custom python script where the lists are built in the first place ("Person_ren.py").
The second tooltip I haven't been able to find where it's builder function is, but I have a sneaking suspicion it's buried in one of the python files in the "map" folder. This one seems like legacy code because some of the hints in the tooltip always appear while others only appear when speaking with a specific character (i.e. when you u lock special traits from Nora). My best guess is that it was primarily used for helping players progress quest that weren't necessarily tied to a character's obedience, love, and lust traits, but Sarah kinda debunks that theory since she has hints in both locations (character sheet and bottom left corner in the map).
The "Event!" function is tied to story events which the player has triggered - whether that be through the right stats or favorable RNG. The addition of another indicator or even showing a warning screen before progressing could be useful if appended to the already defined "Event!" function as any other implementation would double the work for story events.
Luckily I can answer this question! The answer is you can completely skip over characters and storylines. For example, if you utilize trances and change Lily's opinion on incest to be favorable, you can completely skip over Iris's introduction. Additionally, if you don't opt for Nora's route early on with serum testing, you will skip over the following: Emily and Christine's introduction, powerful serum traits, and interns.
You can also completely miss the trigger from Ashley for personal serums by accident or just refusing to hire her. Not hiring Sarah results in several business related storylines being skipped. Not hiring Ellie results in the loss of nanobot research. Not hiring Alexia results in the loss of Kaya's introduction and the ability to hire interns. Hiring Mom or Lily too fast breaks the triggers for their respective storylines.
Furthermore, you can completely miss out on the
brother brothel if you either: don't explore the streets to unlock the building, fail to blackmail Gabriella, fail to invest in the sex shop, or refuse to buy the building. You can also miss Christina's introduction if you don't engage in public sex.
There are some business events that can fail to trigger because of poor RNG, such as unisex bathrooms. You can also skip out on company yoga if you fail to progress Erica's story or cause her to ghost you (which resets her entire questline). Erica is also required to progress Kaya's questline so that serves as another facet of the intern mechanic.
There are a few more mechanics which you can inadvertently skip, but the above paragraphs list out most of the major events. While some players say it's a complex mess because of it, my personal opinion is similar to yours in that it just requires a ton of boring work polishing the already built systems and adding clarity where needed.
Adding a wiki is an interesting idea and has been done for other games of similar complexity. The best option would be setting one up through Miraheze as they definitely allow NSFW content to be posted. Ultimately though, it depends on whether Tristim and Starbuck want to submit a request to the site for obtaining a wiki since they're the current IP holders for the game and can set trusted players up with admin permissions.
Apologies for such a long post, there were a lot of great points to discuss and I wanted to have a comprehensive breakdown of the current state of the game that I can reference in the future.
