To the people saying this is not a problem, it is. In particular, iMessage seems to often get confused when trying to send a picture. The progress bar will get to half or even mostly full, and then just pause ...forever.

It's not a connection issue. On several occasions after running into this iMessage issue, I have emailed the picture full-res without problems.

That said, I don't think iMessage is terrible. I love it when it works as expected.