Did this transition 10 years ago (Brazil). It takes some discipline. I guess the $100,000 CAD is not that good if you are working full time for them (specially in the most expensive provinces) because you will not have time for business development - and having just one big client is putting all eggs in one basket.

In USA health insurance is probably the most expensive thing for a contractor but I guess in Canada you have your bases covered.

My advice is to subcontract other people as soon as possible and invest the extra time to learn about sales, marketing and negotiation, then go after new business. Currency exchange rates are excellent for subcontracting from Brazil or Argentina.

Good luck and drop an email if you want to ask anything.