I never used outlook express, but I do use microsoft outlook. I am not sure if I understand your question, but since no one has helped you, I thought I could at least let you know how I deal with my pictures.
First of all I save my pictures in My Documents with a new folder called My pictures. I just create multiple folders in the MY Pictures with different catagories for the pictures.
Then in the outlook when I want a picture I click on new in the tool bar, for creating a new email. Then I click in the body of the email, which then gives me the option in the tool bar to click on Insert.
Then I click on picture and a box will pop up.
I click on Browse then and I find the My Documents folder and open it.
Then I find the My pictures folder and then I find the picture folder inside that I created earlier that I want to view.
It will open up a preview box with all the pictures that I had placed there. You can double click on the picture you want or click on the open command.
Then it will go back to your new email and there will ba a box. you just click OK and it will insert the picture.
I am sorry if this doesn't answer your question or if I didn't understand.
Sometimes when you switch to other programs, you don't get to have the same options that you are use to and you need to adjust to the new programs.
Maybe some one else with more knolege than I will help you , I hope