Wood shingles can be longer lasting, however it depends on the material, installation and maintenance. Cedar generally last longer than pine for example. Once you have chosen the material (most commonly cedar in Ontario) then there are differing types.
Wooden shingles are sawn whereas shakes are split. Normally both require maintenance, ensuring they are tightly secured along the ridge & removing any moss, algae or lichens that develop. Over time shakes / shingles may split, curl upwards or become dislodged and should be repaired / replaced as this occurs to reduce the likelihood of water penetration.
In general, the life expectancy of wood shingles / shakes is about 20 to 40 years when installed new. This too will depend on the the thickness of the wood as well as the grade of wood chosen i.e. whether they are “clear” free of knots or not. Further, it will depend on weathering and the method of installation utilized such as underlayment for the wood. The life expectancy of a roof will vary depending on many factors. Some shakes / shingles installed with an air gap between them and the roof sheathing may last longer.
Before you purchase a home with a wooden roof or embark on the installation of a wood roof, do your homework first!