Hmmm, good point. I think maybe you should stick to BvS in this case (confusing explanation, sorry. Another try …) Maybe you should treat the loop as what it is: a new season. You could end season 1 with telling about the things you were hunting until the last day before the loop (f.e. if you hunted after your 45th ally, it's a friend you wanted to safe, if you needed the last item for the Letter of Marque, you found the last item to a fantastically strong item-set somewhere and took it with you to the new adventures awaiting you in season 2). And it's not as if you'd loose or forget all things after the loop, the items you loose you just loose, that's alright for any story, and the jutsu you forget you have not unlearned but you need to practice them when you don't have some important missions to hold your attention.
…wow, too tired to think in English, so if there are loads of unintelligible things written, I'll correct them tomorrow
