Project planning--GTD-type questions to ask an elderly person for down sizing?
I am trying to help a friend plan a challenging project. It is proving hard to help someone think about desired outcomes who is focused on the process to the point of only seeing one option. But it has made me realize how easy it is to get fixated on employing a particular method rather than tailoring the process to the desired outcome. This older gentleman has a 23 year accumulation to clean out from his old two bedroom house. He has already moved into a house that is smaller, just bringing the bare necessities. He has about half the living space but has part of a basement for storage, so the total is about 1/2 the size of the first house. The items are books, furniture, family and professional papers, cloths of his and his late wife, photographs, LPs., sheet music, art work. games, band instruments, uniforms, linens, kitchen, etc, and some in order and others stuffed in closets and in piles. He believes that the contents of the piles, closets, wardrobes and china closets must all be sorted out before the items are moved but the sorting out has already taken about six trips and is not complete. I cant tell how incomplete but he thinks two more trips of 4 to 5 days each. It is a day's effort to get from one house to the other, either by plane or train. At this point I would think that the goal of getting the stuff he really needs and wants into the new place and rid of the rest would be better achieved by having it all shipped to a storage place near where he resides and working on it bit by bit. He does not drive and would need to have someone get him to the storage place and help him. Thus far it has been impossible to have a project planning conversation that is productive. He says he wants me to help but I can't get specifics from him. His idea of the next action is when to book the transportation. I think the next action is project planning. But, what questions can I ask that are useful to this end?
By the way. each trip costs about $400.00 in transportation. I would be grateful for any suggestions/ideas.