What is the legal way to add new images into the custom theme and articles?

Hello fellows! First of all thanx to all developers and customizers of this well-designed open source web application.
What I'm trying to do is to add an image into my custom theme.
First of all I have created a copy of "fauxcoly" theme and then started to study it's content. In "Media Files" chapter of my weblog I saw the folder named "icons". In this folder I saw the file named "asf-logo.png". In "Templates" chapter in the template named "standard_footer" I obtained the following tag:
<img src='$url.resource("icons/asf-logo.png")' border="0" alt="Apache feather" />

And on the rendered web page I see the link related to this tag:
http://127.0.0.1:8080/roller/main/resource/icons/asf-logo.png

So I decided to link my uploaded images from my custom theme either by "$url.resource" method or by direct link:
http://127.0.0.1:8080/roller/main/resource/images/asf-logo.png.

Then I add the image named "asf-logo.png" from Tomcat's "webapps" folder using "Media Files" chapter of admin UI. I preserved the current filename ("asf-logo.png") and assigned the folder "images" for it. So I have got two identical files: one in the directory named "icons" and another in the directory names "images". Then I'm trying to access new uploaded file by the url:
http://127.0.0.1:8080/roller/main/resource/images/asf-logo.png

And get 404 error, although the initial url works OK:
http://127.0.0.1:8080/roller/main/resource/icons/asf-logo.png

Accessing file by the model object "$url" don't work either.
What I do wrong? Why is so different behavior for user uploaded files and files copied automatically from default theme? 

Tested on 5.0.1 and 5.0.3 under Tomcat 7.0.27 under OpenJDK 1.7.0_25