I have everything on the main computer and then shift to the laptop to move around with. I find this is easy having done for well 10 years or more I guess. If I want to change something is easy to do as well as to add notes
All the outside stuff is tagged and numbered that matches up to a line that explains it all. I take pictures each year so I can see how it looked months later if I want to maybe change something. Each tote I have has a number and then I have a list of what in that number tote and or box.
Since Christmas and Halloween stuff getting to be to so much I have add as well where it is stored. Then when I get ready I am not going around looking for stuff. Have all year to make your notes and what I call the "make it happen files." To me when you have it all laid out really cuts down on the set and take down time. Plus when your container are marked if you are putting say stuff in the living room up to make room you put it if possible in the container that the decorations came out of. Another thing is if stuff is wrapped or in little boxes if it stays with the container you look at container number and know what goes in it when you put stuff up and all packing stuff right there.
I do the recipe list for shopping as well then depending on what I am going to make I then jusy copy and paste and print and I have my list for the store. I as well try to start in say late September for some items or watching for it on sale to help spead costs out.
To me having it all organized like this just makes it all flow and takes any stress of it all away.
Never worry about the size of your Christmas tree. In the eyes of children, they are all 30 feet tall.