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Did you try sending over WiFi to see if that makes a difference? I've never had a problem on sending pictures at all whether it is to a phone or an email.
EDIT: I used both the stock app, and Handcent which is my preferred text sending app.
Wow, thanks for that info. I did not know ever notice that before and so I just sent a pic to someone and sure enough the 3G icon popped on. I just assumed it would send it by wifi since it is connected to my network.