When I was visiting my brother a couple of weeks ago he showed me a really cool thing. It is a shirt folder. A plastic form for folding a shirt perfectly and very flat. Prior to his retirement he traveled a lot for business so it was really handy.
When he showed it to me he was folding perhaps half a dozen shirts with collars and such. He said "I'm going to donate these to the homeless. They really do like precisely folded shirts."
I tried it with a clean T shirt out of my bag. Worked perfectly. Maybe you need a shirt folder? :)
Those are awesome, @bigtom13. Several of my family members use them for travel. I like the idea of using them for organizing what you need. Maybe that would help the decision making. If it doesn't fit in the the defined box spaces, out it goes!