Is it possible to get both scenes? Also, what scenes do I miss by getting drunk/staying sober?
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Apart from Vilma's scene, being drunk actually lets you unlock the most scenes out of the episode (considering that you're playing the Siren or Kitten routes, of course).
I thought at first that it was best to keep Ashe on the sober side, but it kind of makes sense for her to be tipsy in order to feel encouraged to do certain stuff, even on the Siren path.
As for getting several scenes from those choices, you can't, you're only able to do one out of the four.
What you COULD do is watching how the scenes play out, see the variables involved, and adding them by using tools like URM. That way, the game would register two (or more) scenes from that bunch as experienced.
However, that's something you can do, like I said, but not particularly advisable, as we don't know yet how the different choices could play out in the future, and if they will overlap or even potentially corrupt that save.
What I think (this is entirely my opinion) is that the first two choices (Kimmy/Madison and Wilma) are the ones that could have a sort of 'bigger' impact in the future, as I'm not sure how many interactions there'll be with the strippers/pornstars as things stand out.