I always play with the Storyteller mode on, and that tells me the change in percentages with regard to character relationships, etc. To romance Amanda Chastain, your character needs to say and do things that will built up her relationship status to 70% and over (Friend).
For the last few playthroughs, I’ve usually been playing a strategy of getting Chastain and Monroe reconciled (sometimes by agreeing to the requirements of both vampiresses).
From the author’s tip, it is possible to meet Amanda Chastain early - in Ch.7 - by getting caught by Jayfield, in Bleakrest House. But I can’t recall if it’s possible, here, to gain any points with Chastain to get her to like you. I suspect not.
To my knowledge there isn’t a ‘romance achievement with Amanda’, per se. There is the Blood Kiss Achievement - which the MC can get with her, Jace, or Monroe - provided the relationship status has risen high enough for them to want to have sex with the MC. There’s also ‘Ending 4, the Ghoul Achievement’ - and to get that, you need to get pally with Chastain.
In case you’re not sure, here’s how to get a sexual encounter with Amanda Chastain:
In Ch.9, your character has options to befriend and even flirt with Chastain, thus upping the relationship status between them. In Ch.10, when Perry is breaking into the MC’s house, it’s probably better to ring for Chastain’s help (though if you ring for Monroe, Chastain may get there first anyway). The MC has an opportunity to say to Chastain ‘I’ll help you, if…’ and there’s an option for her/him to ask to become a Ghoul. If your MC’s agreed to help her by the end of Ch.10, Chastain will try to seduce the MC in grandpa’s bedroom. If her status is high enough by this stage, she’ll even offer your MC a taste of her blood. On my last play, after a peaceful resolution between Chastain and Monroe - and with just 20% on Path of Immortality, dwarfed by Path of Knowledge (Path of Righteousness 0%), Chastain invited my MC to Bleakrest House, to offer her the Ghoul Achievement. Avoid anything that upsets Chastain too much. She wants you to like her.
As for reconciling the vampiresses… Aim for a combination of good social attributes and skills with any combined total of 5 or 6 dots, by Ch.9. If you’re already allied with Chastain, she’ll send Jayfield to talk with your MC during Ch.11 - and you can tell him of the thin-blood’s planned attack, if you wish. Tell your human friends that your real aim is to get the two sides reconciled before setting out for the gazebo, then sneak in close to Chastain, and be ready to break up the fight between the vampiresses, persuading Monroe to give up.
Hope that helps!
On a separate note to everyone, has anyone yet found if the Stress levels of your human friends makes a difference in the game? They never seem to impact on my playthroughs. But then I’ve never got any of my ‘hunting party’ killed in the park yet.