[bhxtyrant]

Ah i see.Seems this is gonna be the hardest thing to overcome.Is there perhaps a way i can make a custom BBcode just to control the border?for example if i wanted an image to have the boarder i could do-

[border][url="google.com"] [img]http://mysite.com/image.jpg[/ img] [/ url][/border]

That would be a decent alternative as this doesnt really need to be used on every image.I like your idea better though so that would be prefered if it were possible.

:EDIT:
Cant i use something like this to manage the images via CSS?

.postimage.topleft{background-image: url(test.jpg);}
.postimage.topright{background-image: url(test.jpg);}
.postimage.topmid{background-image: url(test.jpg);}
.postimage.left{background-image: url(test.jpg);}
.postimage.right{background-image: url(test.jpg);}
.postimage.botleft{background-image: url(test.jpg);}
.postimage.botright{background-image: url(test.jpg);}
.postimage.botmid{background-image: url(test.jpg);}