I'm not sure if DoubleK will approve of me replying, as we haven't been with Wind/Freedom for several months.
However your question is one of the reasons we moved away. There were just too many times when outside of the city that we didn't have access. Not even on the roaming options. We had a $33 plan for my son, and the extra $15 we spend per month to go with Koodo (or any of the other secondary providers) is well worth it.
Just 2 weeks ago we were going hiking, and the trail we wanted to go on was closed due to bears. The people in our group on Freedom didn't get the text until 45 minutes later.