The game is really fun! I've gotten most of everyone's achievements but struggling with getting all of Florence's achievements for some reason. Any help would be very appreciated :].
haha, it's really funny that you asked because i helped someone else in the comments with those exact endings not too long ago. i just copied and pasted what i wrote there, so if you have any questions, please don't hesitate to ask! :)
spoilers ahead!
as for florence's 1st and 5th ending...
to get both of them you have to accept the gun from florence when he offers it to you, this happens after interviewing magnolia about the break-in. i believe you also have to ask about the notebook after seeing the strange writing in it. after this, you have to wait an in-game week for florence to come back to town on the weekend. go to the sheriff's office and talk to him and you can ask him to teach you how to use the gun. the shooting lessons are where the endings take place.
florence 1st ending: once you find out about florence's secret at the shooting lesson (you'll find out no matter what choices you make there), he'll kiss you. kiss him back and that will lead to a sex scene and you'll get the achievement.
florence's 5th ending: do the same thing as the 1st ending but do NOT kiss him back. he will not like this and tell you to get on your knees. do not fight back and get on your knees like he told you. another scene will happen and then you will get the achievement!