Can't go wrong with a 4 stroke 250 for a first time rider. I ride a yz250fx and it's my first bike. For trail riding you're going to want to get a headlight and taillight for alberta law. In which case the WR is a good choice. I get by without them though. As long as you keep up with the...
If you're talking about the boots from Blackfoot, don't buy there. They are way to overpriced and you would get them cheaper if you ordered online from the states.
Well you do need a class 6 to ride on the street on your own. My only purpose is to use my dirtbike on trails and apparently, if I want to insure it, some insurance companies require you to have a class 6 motorcycle licence.
I know there are some insurance companies that will insure off-road...