After struggling for way too long, I just gave up and looked at how the whole thing actually worked. I think that you should list the value of the individual answers in your walkthrough, because sometimes there's multiple correct answers, and sometimes there's a definitive wrong/right answer. Here I'll list the results as if I chose the best answer every time. (And just to make things clear, I try to make sure that I not only do things as base Lewis, but don't go around transforming others against their will unless, and only unless they're straight up evil... meaning Tessa and Matthias... Maybe Magnificence. Akarion's a jerk, but he doesn't really meet my standard of deserving it the way being an evil schemer or neglecting one's children does. But even the ones that do deserve it in my opinion, I'm not going to do any really bad transformations because murdering their original selves is way disproportionate in my opinion.)
Sylvie as base lewis: Max 5 points (Mat only gets above 4 if tg'd which I don't do, so this should beat him. Reese gets 8 if male and 5 if female, and a tie is in your favor, so you win as base Lewis but have to TG Reese. I don't have a problem with doing that change because he outright asked me to, so it was consensual, soooo... I guess this is how I ensure that I win without being eeeeevil. Victory is possible)
Azymandia as base Lewis: Max 3 points (Yeah, I'm not even going to bother. Akarion loses if default, soldier, or trophy, and richter needs to be tg'd, but still her normal personality to get above 1 point, so Lewis wins, right? Wrong. Odenval gets either 5 or 6 points and wins unless- and only unless- he's a slug, which is horrible and I wouldn't let that happen even if it was possible outside of the evil spy route, so victory is not possible.)
Vixxy as base lewis: Max 4 points (Gethra loses normally with 0 points but wins if age regressed, Elami loses with 0 points unless she's a spy, meanwhile Magnificence wins with 6 points as male and 7 as female, unless she's been short-stackified or is a peasant, in which case she gets 0 points. Vixxy sure has high standards. I'll consider this as victory possible since you can easily shrink Mag at the very start of the game. But honestly, I think I prefer that she wins. I usually do the harem thing but otherwise leave her as herself in Mingle 3, since that's as far as I'm willing to go, so this is a good way to easily get 12 influence by talking to her immediately after she wins.)
Jonathan as base Lewis: Max 6 points (Base Lewis beats Marazet and Tessa no matter what with a score of 6, Rhianna loses if she's a lioness, wyvern, maid, or princess. The only one of those I think I'd be comfortable with is the lioness one, as that one's consensual I think... but I prefer Rhianna as she is, and really don't like the idea of taking away her family ties, so I'll consider this one as victory not being possible)
Extra note: I think every single date gives an extra three points to buff Lewis, letting you beat literally everyone. If you get the right answers as jacked!Lewis you just... win. ...I actually don't like that. While Lewis is still himself as far as I'm aware, there's just something disappointing about the idea that his physical appearance matters that much. Scrawny normal Lewis deserves love too, and I personally have never seen the appeal of a person's physique as long as they're physically healthy. Seriously... I have never once looked at a supermodel of either sex and understood how they were any more attractive than the average person, though actual unhealthiness/ uncleanliness like being morbidly overweight or physically injured/ sick/ malformed is something I don't find appealing.