I think it's great that you're interested in finding out more about wilderness survival. Based on your notes, however, it does not sound like your band of friends is really ready for a self led expedition. I'm sure that there are organizations in Ontario that foster hiking, backpacking, camping, etc. Here in the Northeast US, I belong to a club called the AMC (Appalachian Mountain Club) that has several local chapters that organize guided trips with trained and experienced leaders. Trips like that allow you to get your feet wet with some experienced folks around to coach you.

In your neck of the woods, maybe check out information from the Ontario Trails Council. Their website has some interesting information. (Makes me want to go up there! The Voyageur Trail in NW Ontario sounds awesome.)

http://www.ontariotrails.on.ca/

It's not that we don't want you to experience what you're asking about... we just want you to do it safely, when you're ready, without reading about you in a SAR after action report.