It's best to get everything done legit, than pay for it when you get caught! Those fines can get very high depending on the officer at the time.
A few weeks ago a few of my friends and I were riding on some trails and out of nowhere there was a "Trail Police". Now one of our friends said he had all his papers done and up to date, but when it was his turn to get checked out what do you know, He didn't have anything at all. The officer said he can impound the vehicle (which I didn't know they can do) but my buddy got nailed with 4 tickets in exceed of $1000.00 in fines. That was his weekend for him, but the rest of us had a blast.
Now as for riding on the rural roads etc etc. I live in the country area outside of Toronto. I was coming our of my drive way as normal, but I swear If I didn't brake sooner this kid on the snowmobile would have hit my front end of the suv I was driving and that would be it for him. Lucky he missed it and was able to stear away from me in time. If you guys are going to ride on the roads and looking for a opening for a trail, please be careful out there. Most people will not see you if you're going fast or if you're sitting now. At least prop up on now kneed and have you're hands on the throttle and brake just in case something happens.