As far as romantic encounters, I can at least help with that part:
Romance Tips
For all romance, you need to note your interest in their respective gender in Chapter one. I thiiiink saying you didn’t like Adam/Salem might lock you out of their respective romances.
Aside from Jace and Chastain, the romances are basically locked in by Chapter eight.
Adam
- You can note an interest in Adam in chapter one - choose that you liked boys and Adam, or that you liked boys and girls and Adam.
- When Adam visits the shop in chapter two, you can express your interest in him if you have either a high Charisma/Persuasion or a high Composure/Persuasion. You can also invite Adam to go with you to Mayor Bumpley’s dinner party.
- In chapter three, if you invited Adam to the dinner party, you can flirt with him.
- In chapter six, at the library, Adam will ask you out if you’ve expressed any interest in him before.
- In chapter eight, you can ask Adam to spend the night with you.
Salem
- You can note an interest in Salem in chapter one - choose that you liked girls and Salem, or that you liked boys and girls and Salem.
- You can ask Salem to move in with you in chapter two
- If you go to the dining room early in chapter three, you get a chance to flirt with Salem
- In chapter six, in the library, you can ask Salem out on a date.
- In chapter eight, you can ask Salem to spend the night with you.
Marcus
- In chapter three, you can accept Marcus’ offer for a hug. Also, if you go into the dining room early, you can sit next to Marcus and flirt with him.
- In chapter eight, during the search for Tyler, you can ask Marcus to go to the tavern with you, and you can ask him to spend the night with you.
Lacey
- In chapter three, if you didn’t invite anyone else, sit with Lacey. You will get an option to flirt with her when the dinner party starts
- In chapter five, you can ask Lacey to dinner when you go to her house.
- In chapter eight, you can ask Lacey to spend the night with you.
Jace
- I’m unsure, but I believe you do need to offer Jace a room in chapter six. Which means that you need to go to Doctor Lobo’s office and meet him, then offer the room.
- If you visited Adam in chapter four and insulted Mr. McCrae, his children will come to beat you up in chapter six. Jace can save you from them, and it gives you an option to flirt.
- In chapter ten, if you rented out the room to Jace, he’ll check in on you. If you have a high enough relationship level, you can express interest in him.
Monroe
- If you side with the thin-bloods, Monroe will come visit you in chapter ten. If you deny Amanda after she visits, you’ll have an option to spend the night with Monroe.
- In chapter twelve, if you defeat Amanda, you can continue your relationship with Monroe or, if you turned her down for being a vampire in chapter ten, you can start a relationship with her.
Chastain
- When Amanda comes to visit you in chapter nine, you can flirt with her.
- In chapter ten, Amanda can flirt with you and initiate an intimate scene.