In the "My documents" in my computer, I created a file:
inside that Family Tree file are 4 files, one for each grandparent and named solely with the surname of that grandparent.
File: Grandparent A
File: Grandparent B
File: Grandparent C
File: Grandparent D
Inside each of the 4 grandparent folders, there is a folder for each surname that is an ancestor to that grandparent including one for the same surname.
File: Grandparent A:
File: Surname 1
File: Surname 2
File: Surname for Grandparent A
Inside each surname folder, I have a folder for every individual of that family who is in my direct line, with the year of their birth in front so as to keep them in order by date.
1716 John Surname 1
1748 William Surname 1
1787 John Surname 1
1812 Henry Surname 1
For Henry's siblings, I put a folder in 1787 John's folder, "Children of 1787 John Surname 1"
All you have to remember then, is which grandparent a surname ascends from. If you can't remember, a quick CTRL + F and you can find it by surname search.
Inside each individual's folder, I put inside all of the documents and photos I find. I name each item first with the year and then what it is, Henry Surname 1 may have the following items:
1787 Christening record, John Surname 1
1792 Will and probate of 1748 William Surname 1
1801 Marriage record, Parsons Parish Church, John Surname 1
When you have a 19th century profile that has 5 census records, marriage, birth death, city directories, will, probate, land records, etc., having them sorted by date makes it easy to track one's movements. If you put the locations in the item names, you don't even need to open the attachments, you can just look in the individual's file and see where they lived year by year, decade by decade just looking at the item's names.