Even loving the side characters like Amy and Sophie, I really wanted some answers from the looping. I mean, there's only two clear hints over the looping, which are when the time froze on the first time and we could hear two voices talking with each other, and another one when MC tries suicide and, technically awake Meghan from the looping. If he actually manage to remove her from the loop it's never known, since it was the last time that she had content IIRC.
If the game has any inspiration on Groundhog Day, as it is obvious, we'll never know the reason on why he's on the looping, but if he didn't improve himself as a person, as he had some glimpses before in the ending of the past Season, he'll never be able to escape.