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You should show a example of question form and question page by picture.
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I think he means a multiple image upload feature, such as here :
http://cksource.com/ckfinder/demo
Using CRTL or SHIFT you can select multiple images to be uploaded

@joel : do you have an issue with CKEditor on www.question2answer.org ? I see that you never use it when you make a question (see field : "More information for the question")
:-) :-)
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I have never tried. But, if you are well customized, this may also be used.
http://kcfinder.sunhater.com/

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