I'd thought about doing what you'd recommended but then it kind of lost the meaning of making the choice in the first place.
It was a way to mend things while also keeping the impact of the first choice.
Personally I don't love games that force players to play it multiple times to see all content. Downloading a 4GB game & only getting 1GB worth of content after playing feels bad.
I'm not against impactful choices, but I guess I don't like to be 'punished,' as you put it, by being forced to give up on a girl.
Kinda why I like yes or no choices (ability to say yes/no to either or both depending on stat/choice checks) compared to either/or choices which only give 1 option.
Guess it depends on how it's implemented, if it feels harsh/punishing & other such factors.
Anyway, I liked the Fiona event, but I hope an early game event doesn't close off Kaylee/Fiona or have too harsh effect on the plot. Also hoping there aren't too many of these harsh choices.
Based on my personal preference ofc, so treat it as such.
As for the lin/leg/des stats - It's pretty much the standard setup that I'd guessed. So 2 advices here:
1. Try to make a good bad path:
The good path is pretty standard & everyone gets it right usually, but the bad path is often not up to par. Even in your description:
"Essentially someone that people would keep their distance from."
I hate it when the bad path is literally so bad, no one likes the MC, all he has are whores etc. I'd for once love to see a good bad path where the MC doesn't loose his brains & insult everybody & turn them away from him.
A lot of scummy people have followers & are liked by many, even though undeserved.
Be great to see a clever, manipulating MC managing to create dependency without using just fear & brute force, who isn't hated by all.
Actually the grace dialogue gives me hope for this, how he manipulates her to divide her from her friends & hopefully plan to fill that void himself. Or how tor_break seems to be about lowering her self esteem so she goes along with MC's (future) abuse.
Or for Eliza path, instead of pure blackmail, once the vid is used to bring her to the MC, he goes all charismatic again, saying the blackmail was just a bluff, leaving her confused & guessing & open to his manipulations.
Basically hoping the _des MC is fleshed out & not one dimensional, more like real scum who people don't hate cause how good they are at it(manipulation/charismatic/acting), instead of rude/selfish idiots who people hate. Just something to think about, no pressure.
2. The middle paths seem to be lacking rn. You have to go all in on resp or rude or you won't be getting to the high checks (like 20 for lili). How about some alternates for ppl whose rude & resp are not very different (14-17).
Same with legacy. It currently plays no role & everything is decided by lin vs des.
How about:
if lin==des or (leg>=lin and leg>=des):
You get to choose from both options
elif lin>des:
Good path option
elif des>lin:
Bad path option.
Anyway, that's just my thoughts. Great if it helps, ignore if it doesn't.
Looking forward to the updates, will try to give feedback.
Game still feels young/short/introductory. Will review once the plot & route structure becomes more apparent.
Good Luck dev