I had that issue with handcent also. I could never get it to send pictures, no matter the strength of the connection, type of data connection, or even state I was in (Oregon or Florida).
It's too bad, I liked it a lot but I didn't want to switch back and forth depending on what kind of message I was sending, so I went back to the stock one (in the Eris).
Since then, I haven't really missed handcent, It occured to me I just need to read the message, I don't need to look at the colors. I also like that I got the popup back on my lock screen without having to use SMS popup.
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