Hi
CodeBlue
My main e-mail account is AOL and I have used it for several years (I have just upgraded to AOL7 in the UK) and have only had a few problems over that period in receiving .jpg pics. The problems were returned mail from either hotmail or I think a yahoo account (I maintain a webpage of pics for Japanese Shiba Inu dogs and get pics sent from all over the world).
Best advice is for you to reduce the density of pic perhaps (if your pic programme has web-ize option) and for your friend to go to AOL Keyword TechChat and speak to one of the online tech support folks - they are there until midnight every day and are very helpful. The Keyword option is findable on top button bar of AOL.
Hope this helps.