Turns out I wasn’t too far away from the end in Play Report (1). In fact I was only about two playthroughs from the end, since the amount of repetition this game has actually makes the true ending very easy to get. It also helps that Vivi happened to be just there in the first dungeon I entered on my true ending playthrough and I managed to recruit her, never having time problems ever again.
I haven’t reached the second half of the game yet but I did do four “playthroughs” so I felt like I should write something here. I’m trying to clear Vivi’s request on the 5th (current) round but if I fuck up I’m not sure if I want to play another round to try and unlock the real deal events.