Grammaretto, sixteen rooms in two months is not a decluttering job, it is a removals job, and the thing that will wear you out is not the lifting but carrying the plan in your head at three in the morning. What has worked for people going from a big house to a small one: sort by destination, not by room. Five lists and only five: DD's trailer, the sale, the shelter and the vet, the tip, and the new house. Walk through once with the phone in your hand and say it as you go, 'landing wardrobe, sale', 'towel chest, vet', so it is out of your head before you reach the next door.
A notebook does it, Google Keep does it, a phone app such as XNeuronal files what you say under each room and can hand the DD list to your daughter before the weekend, so she arrives knowing what is hers and the trailer fills in an hour.
karmalady is right about the suitcases: the whole case goes, they sort it at home. The calendars are your diaries, so they stay; fifty years of them fit in one box, which is more than can be said for the towels. And whatever comes to you in the night goes on the list, not back under the pillow.