You might be emotionally invested in DoL's character during your first few playthroughs, perhaps. Sooner or later you'll come to realisation that all the characters are not much more than H-manga tropes, just as silly as FreeCities' acts of debauchery and sex crimes. You stop caring about Robin the moment you realise that the game allows you to date them and Avery and Whitney and Sydney and Kylar and Alex all within the same playthrough. No genuine attachment, no drama, no nothing. Robin sees you working in the Brothel, you agree to go home with them and five minutes later, you can return to the Brothel to resume prostituting yourself, business as usual. They're just intentionally unfinished, repeatable scripts in the game triggered at certain times of the day with certain criteria met. None of the characters are properly developed. They're vague with no agency of their own, just hanging around here and there. Is Bailey really that much of a threat? They're just minding their own unspecified business, demanding payment every Monday morning now, the payment which is ridiculously easy to refuse, just say you're sorry and moan or kiss for 20 rounds. They will orgasm. The other onlooking orphans will laugh. You'll get dressed and fuck 3 customers as you're selling flowers and potatoes on your way to school. Or not, your choice.
So dark...
It all depends the internal limits you set yourself, or how much you allow the game to affect your morals / views. Don't get me wrong, we are on a porn-gaming forum, choosing to play a game built on the concept that every sexual act is a fight - so we all are dysfunctional to some degree.
But ultimately it boils down on how you chose to play it. For example in my current playthrough my character (average female normal diff, no cheats) is virgin, have over 1k molestation (Graceful), 0 rapes, no crime or exhibitionism fame, never met Alex, Eden, Ivory Wraith or furries, angel, innocent, best student, 400k+ money and the only person she had sex with is Avery. A "good girl". All that effort because she's the only character I care about.
You are treating things from the position "it's just a game, they are all just pixels". I don't know if you had the curiosity to dig in game files, but I did. It's quite painful to set even those
vague NPC's, and their limited agency. I tried for like 4-5 days (10-12 hours/day) to set up a credible NPC that offer the option to brutally remove two named NPC (Whitney and Kylar) and pretty much take their combined place. No Bailey because "can't touch a made guy, would anger the Family" (as in Cosa Nostra family). The set up was easy... the credible part made me abandon the project (and of course the sheer amount of coding required, not to mention English is my 3rd language).
Anyway, my point is every one of those important NPCs (love interest) are pretty credible and distinctive. They are cliché(s) of course but again, there is a tremendous amount of work involved in their shaping / creation. I'm NOT a fanboi and there are plenty of things I don't like / agree with about this game but it's fair to give credit where the credit is due.
Cheers.