Hello,
I am having the same problem with my Droid Razr MAXX. I am not able to attach pictures to text messages through the Gallery. This has been an issue for a few months now, since changing to Ice Cream Sandwich.
My Wi-Fi is turned off. Whenever I try to attach a picture (of any size) it gives me the following message: "Automatically resize picture before sending? Animation my be lost!" I agree, by clicking "Resize." Then it immediately gives me the message "Message size limit reached. Sorry, you cannot add this picture to your message."
Please help! - K