I just bought a I phone 5s with futureshop and it haskoodo as the company. I'm on a medium tab, and I'm paying 35 bucks. I tried to send a image on text but it didn't work, don't we get unlimited image in texts included in the 30 dollar plan?
Your data needs to be enabled for picture messages to send. You wont be charged for the data since picture messaging is free, except that it needs to use the data pipeline.
Your best bet is to connect to a strong wifi source and then turn on data to send and receive any pictures. They turn data back off to ensure no unexpected background data leakage occurs (as they always tend to do).