This will just be a quick guide....

For Isla Endings, choose all the top options.

For Lexi Endings, choose all the bottom options.

SAVE WHEN SUBMITTING YOUR CPS REPORT BECAUSE YOU NEED TO RELOAD FOR EACH CHARACTER ACHIEVEMENT (you can save when clicking on a different option instead of submitting report, it goes right back to that screen)

The Correct answer is Madison Rowville > Financial Gain.
For the other achievement, reload and choose any options other than the one above.

Then start a new game and do it again with either Isla or Lexi whichever you didn't choose at first.