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Think it's better to make a new thread, I guess Ashley has a portrait and Sarah doesn't? After playing it a little more I've noticed one has a portrait and the other is "text box"

I've gotten as far as "everyone starts off on the big adventure (to Badon)" and I'm wondering if there's any problem with spending like 3 weeks just building everyone's trust up and learning new stuff (and sex battles with Ashley). Think it would be a good way to get skills up and trust up now, but not sure if there's a punishment to killing too much time doing so,

Correct, I started the game without a budget so I've been relying on Patreon to pay for art. Sarah's art is actually in progress now, but may not be until 0.18 depending on how schedules work out.

There's no time constraint currently. Time tracking is mostly to give some sense of duration to the adventure, though in some future content there may be time limits (ex. 7 days after you start a quest to finish it). But in general, you can just do whatever you want.