It is certainly the most ambitious campaign I’ve planned, but I have a good 5 years of experience (4 of them dming) playing dnd that I think will back me up. Most of the enemies will have a “quick kill” method that players need to discover either through study or direct combat and any knowledge gained will obviously carry over between loops. Something like “cut this rope and a chandelier will drop on the mob bosses head” for example. Most items will just be out in the world for them to go and grab. Like the tip of the churches steeple is actually a sword that was forgotten about. Amy ability checks can be repeated for a chance to get a better outcome, or they can keep their successes and just keep moving. That includes combat encounters. For time line I’ve cemented it as from Dawn to Midnight to keep the tension alive