there was a time and place several years ago that your post would be my post!
Several of your points are asking too much for what can be programed and can be considered cost effective!
you have several errors in the girls quests!
for miss winston if you visit with buddy or Ayshel or another unique NPC you get to spitroast her,
this enables you to grow your copulation skills greatly, even if they are high already!
later on when leaving the city hall in hamilton you are attacked by a group of payed rogues to leave her alone!
So i assume there is a secret suitor to her and her questline is probably far from finished!
it might have ended for me since i am married already, but for an unmarried MC perhaps there is that questline...
for Adrianne and Michelle questline, if your faction is over 25 in strenght, you can challenge him to a fight and
the preacher backs down, imediatly provides you with a 5 standing on his house which probably provides you with some wealth!
not sure about that part,but then again my MC is a profound Catholic
and as gifted over 5000 merchandise to the church and never seen 1 penny back as contribution!
might be because i refused to provide my golden challice of frankish origin to the church
(this was a nice touch... "frankish origin", implying it might be a relic of the 8-10th century imitating the holy grail)
some of your requests are undoable, but i understand the spirit in which you do it,
as stated several years ago, before i was this jaded your post would be similar to mine!
that being said, how come someone who is not jaded enough ends up in such a forum?
So with the quests, I've tried going to Miss Winton just now with Ansel and Bud, and I don't get a spitroast scene. My guess is that you only get this scene if you previously asked her to pay with other means.
With Adrianne and Michelle, you're right about being able to challenge him, I forgot about that. That said, as far as I'm aware, the player only gets the option to challenge him if they are powerful enough when they first talk to him. The player doesn't have any option to build their strength and come back later.
As for the feasibility of what I'm asking for, I'm assuming you're referring to the automation or the economic improvements. I'm a professional software developer, though with minimal UX experience, so I can speak to the (non-UX) programming aspects of this. Ultimately, nothing I've described is technically complex. While I haven't done a detailed cost estimate, and such an estimate is not possible without more precise requirements, I'd guess that the (non-UX) development of a minimally ambitious set of requirements represents a few hundred hours of work. I'd be surprised if the rest of the work took more than a few hundred hours, though I can't speak authoritatively on that. Now obviously, for a game like this, this still represents a lot of time/money, so the development of these features, especially the economic improvements, are unlikely without significant player demand, but I wouldn't go so far as to call them undoable. It really comes down to how much the player base wants these features and whether Grimdark sees them as being compatible with his vision for the game.
I'm sorry you're so jaded. I know life can be really fucked sometimes. I hope you're able to get yourself to a better place. I know you didn't ask for advice, and I don't mean to be rude by providing it, but I see this perspective a lot online, and I'd like to take a moment to address it, if not for you, then for someone else who is in a similar place. Frankly, my life has been pretty fucked over the past few years, and in part I'm writing this for myself.
In my experience most people who are jaded are jaded because they don't recognize the extent of their own agency. Sometimes people confuse critical thinking with cynicism, and they don't realize that critical thinking includes thinking critically about your own cynicism.
Maybe they have a shitty job, but they don't think they can get a better job so they don't try. Maybe they believe that all employers suck, or that they don't have and can't acquire the skills to get a decent job. They don't realize that good employers exist, and or that not all good jobs require years of complex and expensive training.
Maybe they're in a shitty marriage, but they don't think that they could get a better one, so they don't try. Maybe they don't believe that they can fix their current marriage. Maybe their marriage is truly unfixable, but they believe that all women suck, that they're not good enough to get a good women, that the divorce courts would ruin them, or that being single is worse than being in a bad marriage. They don't realize that good women exist, and that most of them just want a man who treats them decently and acts responsibly. They don't realize that the courts aren't actually rigged, and that being single isn't that bad.
I don't know what your situation is like, but I do know that except for a few extreme situations, everyone has agency. Maybe you can't
guarantee yourself a good life, but you can increase your odds of one. Sometimes things outside of your control will hinder your plans, but if exercise your agency to its fullest, you can maximize your odds of overcoming them. Life can be really fucked sometimes, but if you think critically about your situation, you can almost always find a way of working towards a life that's less fucked.
As for my lack of jadedness. I'm here because I like porn and I like games, and I especially like this porn game. Not everyone who enjoys these things is jaded.