Just to clarify as a Canadian, a Tourist Visa allows 60 days which can be extended for another 30 days for a fee then you can leave the country and re-enter by either land or air under the Visa Exempt program which allows for 30 days plus it can be extended for another 30 days....which would take care of winter...
TLDR : Answer Summary
A Canadian can efficiently manage their stay in Thailand during winter by initially obtaining a Tourist Visa, which allows for a 60-day stay that can be extended for an additional 30 days. After this extension, they can leave and re-enter Thailand using the Visa Exempt program, granting them another 30 days, with an option to extend this by another 30 days. This strategy can help cover most of the winter months in Canada.