1. Play through the game normally. Pick the paths in whatever order you want
2. Repeat step 1, but this time there is different dialog and you can skip past the old ones
3. Start a 3rd playthrough, and select one of the options. This will close the game and nuke your save
4. Turn on All Text in settings, and skip through all of the dialog until you get to your 2nd third playthrough
5. Select the option you didn't pick last time, and read the new dialog
6. You did it! You now should have all of the achievements. If you don't, try again. It shouldn't take too long with All Text enabled