Questions for a new person

Private land requires insurance even with permission and also a green plate. Only place insurance is not needed is your own property.

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I assumed he meant his own land, but thanks for the clarification

At this point, just get yourself an M2 and an old pickup there are lots of dirt cheap dirt bikes that are cheap to rebuild for about $300 after taxes because they are 2 stroke and only have like 7 moving parts versus a 4 stroke which are usually close to $1000 minimum on the smaller bikes.

People are going to throw around numbers on here that may or may not be accurate. I couldn't picture a 250 being 6k-10k for insurance/year at the age of 16. If I were you, I would write the M1 and book and MSF course and if you pass you get your M2. The reason is because the M2 last 5 years and a lot of the restrictions are lifted and it's cheaper on insurance. If you want a motorcycle, might be time to consider getting a part-time job to help pay for the insurance if you go this route. As for insurance, the only place that would insure me was TD insurance. I was 19, had just gotten my M1 and didn't have any other license. For my first year, I paid 3800 on a brand new Honda CBR 250RA with a riding course. Now two years later, Im paying 1900/year for a DRZ 400 SM with a clean record.

try to convince your dad to get his license and get the insurance on him, and you as the secondary. your rate will decrease significantly. Insurance is a scam in ontario...and you don't lose anything by not having your own insurance