Texting iPhone 5 to iPhone 5 (roaming) I am ready to pull my hair out.  My boyfriend and I both have iPhone 5's and live in Canada.  When he is here, there is no problem.  But when he travels (which is very often) to the States, he is not getting my messages and I am not getting his - at least inconsistently.  HE gets texts from everyone else but me it seems because they are not using iphones. It shows that my messages were sent from me (no errors), but they don't get to him, and viseversa - he is also sending some to me when he is away, that I am not getting.  What in the world is happening?  

I thought it would send them to one another as an SMS if iMessage was unavailable but evidently not.  But I just noticed a setting that was OFF on mine that says "send as SMS when iMessage isn't available".  When did this change? I thought it would automatically do that?
You basically answered it yourself. Your iPhone is trying to send iMessages and can only deliver them when he has internet access (apparently he turned data roaming off). What you also can do is click on the message in the blue bubble, hold, and then select "sent as text measage". This will convert the iMessage to an SMS and it will appear in a green bubble.