Content Library icon display question

AncientWire

Today I decided to begin work on my content library.  I thought about how to arrange everything and setup a bunch of categories and sub categores.
I went to Products and started at the top.  Right click, Create Category From, highlight the items within the product, choose the location.  On to the next. 
I have noticed that when I click on my Vehicle category it shows the contents of the first product listed, which is Vehicle / Cars&Trucks / The Product. 
I removed the first one just to see, and the second products items show up.
When I click on my Buildings category, it does not show the contents of the folder until I get down to The Product.  Screen Shots Attached.
I can see this being either very helpful or just completely over the top information overload. 
I created both of the main categores.
What is different?  How can I stop it or make it happen at will?
Thanks!
Helene